This is the second post in the series…. the first one When to hire your first Chief People Officer is here).

While all CXOs are important to a company, the Chief People Officer is the one role you don’t want to get wrong because People Ops impacts every facet of a company. If you hire the wrong people—even one wrong person—you’ll regret it, and so will everyone else in your company. If you short-change the onboarding process you’ll create tons of work for others in the company to answer questions, teach people the systems, and help them get up to speed quickly—not to mention the frustration of the new hire. And of course, if you or your employees do anything illegal, discriminatory, or harassing, you’ll end up in legal trouble and you’ll lose—big time. So, it’s not enough, if you’re expanding rapidly, to “just get a Chief People Officer,” you need to hire a great Chief People Officer and I have found that great Chief People Officers do three things particularly well:

The most important characteristic or attribute of a great Chief People Officer is that they believe their function is strategic. In Startup CXO Chief People Officer Cathy Hawtrey wrote about the ways in which HR/People can be a strategic function and not just a tactical corporate function.  It’s true of most functions, but for whatever reason, (likely past experience), HR leaders frequently don’t view themselves or their functions as strategic, which is not only a huge missed opportunity but maybe says something more important about the confidence level of the Chief People Officer.  If that’s their frame of reference, then they will likely be tactical managers, they’ll keep the trains running on time, but you won’t be able to anticipate the changing talent landscape, much less be strategic about it.  If they believe they can move the needle on the business by improving engagement and productivity and efficiency, if they believe they can make the executive team more effective by helping you with team facilitation and coaching…they can do anything.

A second important characteristic of the Chief People Officer is courage—they have the courage to call you (you, the CEO) out on things directly and firmly when they see you doing or saying anything that is a bit off. It could be around language, inclusion, values, authenticity, or anything else, but they don’t let it slide or ignore it. The CPO, along with you, are the principal stewards of the company’s values and culture.  Even the best CEOs benefit from having a watchdog from time to time.

A third critical trait of a great Chief People Officer is that they think about investment in People in terms of ROI.  It’s one thing to run a killer recruiting function and fill seats efficiently, with high quality, as asked.  It’s an entirely different thing to start the recruiting process by asking if the role is needed, at that level and compensation band, or whether there are other people, fractional people, contractors, or shifts in lower value activities that could be put to work instead.  Only heads of People with deep understandings of the business can transform the function from a gatekeeper/”no” role into a business accelerator.

A great Chief People Officer is all of these things—strategic, courageous, and financially astute. Above all, great Chief people Officers know that they are the role model within a company and that their behavior, their language, their inclusiveness is setting the tone and providing a template for others to follow. 

(You can find this post on the Bolster Blog here)

(This is the fourth post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, and 3.)

Monday, March 23, Day 7

• Wellness screening – put hot cup of coffee against my temples – now finally the thermometer works (although I can’t say that it gives me a high degree of comfort that I have figured out a workaround!)
• Furious execution and still backlog is growing no matter how much I do – thank goodness team is growing.  Never seen this before – work coming in faster than I can process it, and I am a fast processer. Inbox clean when I go to bed, up to 75 when I wake up, never slows down
• Private sector explosion – this guy can print 3D swabs – but are they compliant?  This guy has an idea for cleansing PPE, this guy can do 3D printing of Ventilator replacement parts, etc.  How to corral?
• Corporate Volunteer form is up – 225 entries in the first 12 hours – WOW
• Congressmen and Senators – people contact them, so they want to help, they want to make news, not coordinated enough with state efforts
• Jay Want – early diagnosis losing sense of smell – low tech way to New Normal
• Coordination continues to be key – multiple cabinet level agencies doing their own thing while multiple private sector groups are doing their own thing (e.g. App – “everyone thinks they’re the only people who have this idea”)
• Mayor of Denver just announced lockdown, I guess that trumps the state solution in town, maybe it’s ok since that just leaves rural areas a bit fuzzier
• Need to revise OS – team is about to go from 3 to 9, private sector spinning up
• Brad OS and State employee OS are different – Slack/Trello/Zoom are not tools state employees are familiar with or can even access.  Now what?
• Kacey insists the team works remotely other than leaders and critical meetings so we can role model social distancing.  GOOD CALL
• One of our private sector guys goes rogue on PR, total bummer – this part (comms) about what we are doing could be more coordinated for sure, but not a priority
• Lots of texts/call with Jared, such a smart and thoughtful guy, really interesting

Tuesday, March 24, Day 8

• Been a week, feels like a month
• Fluid changes to both OS for team and OS for private sector group
• Zoom licenses – state will take a couple weeks to procure them, gotta work around it with Brad
• Slack app won’t get through the firewall.  Maybe IT’s supervisor can do us a favor?
• Comp – interesting expedited process – normally takes 65 days to get approval for temps, today we got it done in an hour!  Comp levels seem incredibly low. But we got done what we needed to get done
• Some minor territorial conflicts with state tech team and our private sector tech team.  Will have to resolve. Surprising how few of these there have been so far given that our team is new and shiny and breaking rules
• Big new Team meeting for first time with Sarah in lead, Red/Yellow/Green check-in (I like that – may have to borrow it!)
• Starting to feel obsolete – love that!  Sarah crushing it, totally feels like the right leader, need to make sure she has enough support (might need an admin?)
• Also…maybe I’m not feeling well?  A little worried I am getting sick. Hope that’s not true, or if it is, hope it’s not the BAD kind of sick.  Going to go work from hotel rest of afternoon
• Call with Jared – concern about managing state’s psychology – testing and isolation services
• Prep for press conference tomorrow

Wednesday, March 25, Day 9

• Woke up feeling awesome – phew – hopefully that was just fatigue or stress induced
• Sarah drowning a bit, feels like me on my 3rd day so makes sense
• Reigning in and organizing private sector seems like a full time job.  We are going to recruit my friend Michelle (ex-RP) to come work with Brad on volunteer management. HALLELUJAH!
• Whiteboard meeting with Kacey holding up her laptop so they can see it on Zoom – hilarious – technology not really working, but we are making the best of it
• State role – facilitate alt supply chain to hospitals since normal chain is broken…also maintain emergency state cache – complex but makes more sense now
• More territorial things starting to pop up with state government…processing volunteers
• Comms overload – here comes the text to alert you to the email to alert you to the phone call
• This team/project is clearly a case of finite resources meets infinite scope and infinite volunteer hand-raising
• Gov press conference – issues Stay at Home order through April 11 (interesting, that wasn’t in the version of the talking points I saw several hours before)
• Meeting some of our new team members.  I can’t even keep up with them, I think we’re up to 15+ now.  Kacey and Kyle are recruiting machines and all these people’s managers are just loaning to us immediately.  Love that.
• Amazingly talented and dedicated state employees – seem young, probably not paid well, but superior to private sector comprables in some ways 
• Talk with Kacey and Sarah about staff/not drowning
• Kacey feels like Sarah is doing a great job, so she cleared me to go home (wouldn’t have gone without her saying ok, she understands how this whole thing is working way better than I do – I guess that’s what a good chief of staff does!)

Stay tuned for more tomorrow…

(This post also appeared on Bolster.com).

As we wrote in The Gig Economy Executive, the major societal trend to “gig,” or part-time/freelance work, has reached the C-Suite.  We created Bolster to help organize a talent marketplace out of what is mostly an informal economy today – one where VC- and PE-backed companies find trusted freelance executives and consultants from their networks.  

In that earlier blog post, we wrote about the different types of on-demand executive work that C-level executives engage in:  interim, fractional, mentor/coach/advisor, project-based consulting, and board roles.

As we’ve been building Bolster this year, we’ve come to appreciate that not only are there different types of gig economy roles…there are several different archetypes of gig economy executives, too.  While there is a clear common theme of the desire to do some form of freelance, or non-full-time work that cuts across the four types, they are very different in their stage of life and their needs.  These are our four main Member user personae, to use the language of Product Management.

First, there is the In Between Executive.  This is the original concept of our founding investors at High Alpha and Silicon Valley Bank that drove their interest in Bolster.  The In Between Executive is someone who is generally mid-career and used to working in full time C-level roles and is, for whatever reason, between jobs at the moment.  Maybe her company just got acquired and she is taking a break.  Maybe her company restructured her out of a job.  Maybe she needed or wanted to take a break from work for family or health reasons.  Maybe she was just ready to look for a new career challenge.  The In Between Executive is perfectly suited to any of the on-demand executive role types but is a particularly good fit for interim CXO, mentor/coach/advisor, and project-based consulting roles.

Second, there is the Career On-Demand Executive.  The Career On-Demand Executive is usually someone who has had many years of experience as a full-time executive and who is now looking for something more flexible, or who just enjoys more variety in his work.  One of the Career On-Demand Executives in the Bolster network I spoke with early on described her journey to me like this:  she was “between things” when a friend of hers who had moved to France and started a company asked her to come set up her HR Department and run it for 6 months while hiring full-time staff.  She took a month off, lived in Paris for 6 months, took another month off, then started to look for something else like that.  Ooh la la.  Sounds pretty good to me.  The Career On-Demand Executive is a particularly good fit for interim CXO, fractional CXO, and project-based consulting roles.

Next, there is the Not Retired Executive.  When I think of the Not Retired Executive, I think of my Dad, who was a successful technology entrepreneur for 30+ years.  Since he sold his company several years back, he has helped a number of startup CEOs do everything from raise money to build a sales and marketing plan, to manage supply chains.  Sometimes he gets paid in cash as a consultant, sometimes he gets equity as an Executive Chairman.  Sometimes he talks to younger entrepreneurs and helps them out “just because.”  The reality of the Not Retired Executive today, however, is that many people are “not retiring” younger and younger because they’ve made enough money to take a step back from hard-charging full-time jobs.  The Not Retired Executive is perfectly suited to any of the on-demand executive role types.  The ones who are later in their careers and closer to being actually retired are particularly good fits for mentor/coach/advisor and board roles.

Finally, there is the Side Hustle Seeker.  The Side Hustle Seeker is someone who is a full-time executive somewhere but who is looking for additional professional opportunities.  She may be an experienced CMO who is excited about mentoring up-and-coming marketing leaders via a local or industry-based professional organization.  She may be looking for chances to “pay it forward” because someone mentored her along the way, earlier in her career.  She may have accumulated enough experience and wisdom to be ready for her first board of directors seat.  Regardless, she’s someone who is a “high wattage” professional who wants to learn and grow herself by connecting with others outside her day-to-day role.  The Side Hustle Seeker is best matched with mentor/coach/advisor and board roles.

So, what kind of gig economy executive are you, and how can Bolster help you find the kind of work you’re looking for while providing you with tools and resources to simplify your life?  Join Bolster as a member to find out!

(This is the fifth post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, 3, and 4.)

Thursday, March 26, Day 10

• Sarah continuing to take over and stronger by the day
• Sarah cleared me to go home, only one more person to ask
• Deep deep dive on Mass Testing – so good to spend that time 
• Pretty much got the strategy right – shocking we could get that close with so little public health experience – Kyle awesome – EOC leadership briefing
• That was most of the day
• Some downloads to Sarah and Kacey
• Feeling that two of our project teams are going sideways – that will be a big focus for me tomorrow before I leave
• Quick assignments for tomorrow
• Talked to Jared – he’s good with me going now that Sarah is in place and things are running.  Awesome!

Friday, March 27,  Day 11

• Download with a couple of the project teams to help get them back on track 
• This whole thing is one big exercise in Agile!
• Serendipitously might have found private sector partner for one of the teams in need.  Reminded of George’s great line, “when the student is ready, the teacher appears”
• Gov briefing on mass testing plan
• Spent a lot of the day on strategy/overview/retrospective deck.  Have to review it with Brad and core team members. Gov wants to get it in front of the National Governors Association to share learnings/best practices for the states behind us in this fight
• Gov thankful goodbye
• Brad thank you Haiku – so awesome – “You see things others don’t see”
• FInal team check-in, lots of nice thank yous from people on team
• Close out drinks with Sarah, Kacey, Kyle – persevered despite lack of corkscrew.  Poor Kyle’s shirt looks like he was standing next to a shooting victim
• Incredibly thankful moment with team – really like and care about these people – we’ve done such great work together – 11 days but feels like months and months
• Close out email to Governor and Chief of Staff about team

Saturday, March 28, Day 12

• Check out!  Fly home! Happy to see Mariquita, Casey, Wilson, and Elyse!

Stay tuned for two more wrap-up posts, tomorrow and the next day…

(This is the sixth post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, 3, 4, and 5.)

As these posts have been running, a few people have asked me to quickly compare this experience to the experience of being a Startup CEO.  And that’s an interesting way to think about it. In a lot of ways, the couple of weeks of getting the IRT up and running felt like starting up a new business, only a lot more intense.  Following the outline of sections in Startup CEO:  a field guide to scaling up your business…

Part One: Storytelling.  The whole timeframe was super compressed.  It took us 2 days to be able to spend 4 hours writing our initial pitch deck defining scope, structure, and staffing request – and that was while we were working hard on our first two workstreams.  In a startup environment, that process would have taken much longer, involved more customer discovery and product/market fit research and spending 100% of our time on that. But then we got our “approval and funding” in about 45 minutes – that would have taken weeks and involved dozens of pitch meetings.  In terms of creating the organization’s Mission, Vision, and Values, we didn’t even bother, although I think it helped that the three of us were generally on the same page with how to work and that urgency was the essence of our job. The larger emergency operations team that we were more or less embedded in also had a very clear set of values and operating principles on display…although we didn’t actually go read them, I think they were in sync with our view of our team’s mission and principles.  In terms of “bringing our story to life,” that was wholly unnecessary!

Part Two: Building The Company’s Human Capital.  Like a startup, getting it right with the first handful of employees means everything.  In this case, the first two deputies on the team, handpicked by the Governor’s staff, were awesome and critical.  Bringing someone in from the private sector to run a public sector team only works when the rest of the team is incredibly knowledgeable about how the machinery of state government works.  And in the end, I think Sarah will be a better leader for the team than I was because she had a combination of private and public sector experience (and within her public sector experience, she had a lot of emergency response experience).  In general, the recruiting process was soooo different than private sector and public sector normally are. The first two team members handpicked the best people they knew in other relevant parts of the government. People were brought onto the team after one short phone call.  Other state departments heads loaned their people willingly. No such thing as a comp negotiation or a reference check. There were a bunch of other things under the “Human Capital” heading that are interesting notes/comparables as well. First, feedback in a compressed-timeframe emergency is something that you absolutely can’t skip – and you can’t wait for a formal process either.  Our team was pretty good about giving feedback at least daily in a semi-structured way as well as in the moment. We didn’t really have time to get into things like career pathing and compensation and firing. We did, after about 6 days at the suggestion of Kacey, our Chief of Staff, move the team to almost entirely remote (other than leadership and occasional critical meetings). This worked surprisingly well for a workforce probably unaccustomed to remote work.  The rest of the world is also learning how to do a lot of that now, too.

Part Three: Execution.  This whole experience was 97% execution.  In fact, we had a hard time finding time for things like strategy and planning because there was a crushing amount of work to do (welcome to emergency response), and a small team to do it.  We didn’t have to worry about raising money, budgeting, forecasting, reporting, and some of the other major execution steps in the private sector. We did do a good job of creating goals and milestones for our workstreams, but even that took a couple of weeks, and in retrospect, I wish we’d been able to do some of those sooner.  In terms of how our work got done, we were very conscious of creating daily meeting routines to structure our day and work – but there was no such thing as even a weekly meeting (let alone monthly strategics or quarterly offsites!), only daily meetings, multiple times per day. One thing that was interesting – I talk in the book about being deliberate and consistent with your platforms, especially around communication.  Channel proliferation is a real issue today (much more so than when I wrote the book), but we had an interesting mismatch at the beginning. The public sector team was used to email, text, and Google hangouts for comms. Nothing else. The private sector team used those things but was a lot more comfortable with Trello, Zoom, and Slack. Thank goodness both teams used G-Suite and not a mix of that and LiveOffice. But getting everyone on the team to converge on a couple systems is a work in progress and was messy, as evidenced in this great moment where Kacey was holding a laptop up to an actual whiteboard to show one of our private sector teams how she was thinking about something. 

Part Four: Building and Leading a Board of Directors.  This is kind of N/A, although the proxy for it in our case on the IRT was the leadership structure of the Emergency Operations Center and then the Governor and the part of his cabinet that was keyed into the emergency response.  In this regard, the main differences between the private sector and public sector were speed/formality (no room for formality when you’re meeting daily or at a moment’s notice!), and, interesting, the need for integration. A company reports to its board on how it’s doing.  This team had to use its “board” to make sure it was integrating with other state agencies and initiatives. In this way, the team functioned more like a business unit within a company than an actual company.

Part Five: Managing Yourself So You can Manage Others.  This was obviously critical…and obviously quite difficult.  And within the overall Emergency Operations Center (outside of our team, the real emergency professionals), there were people, including leaders, who were working 7 days/week for multiple weeks on end, and long days, too.  At one point, the EOC leader posted this note on the wall, and he frequently took time in daily briefings to encourage everyone to take a day or two off and take care of themselves physically.  He role-modeled that behavior as well. You can only run a sprint for so long. Once it becomes clear it’s a marathon, well, you know.

Stay tuned for the final post in the series tomorrow…

I haven’t taken a poll to figure out the overlap between people who read this blog and people that bought the first edition of Startup CEO, but I’m guessing there’s a high degree of it. If you are familiar with the book, I don’t want to bore you with a recap of what I wrote, but I thought I would devote the next several blogs to new ideas in the second edition. First, the new cover art from the publisher is kind of cool:

The first question you might have is, “Why a second edition? Didn’t you say everything you needed to say the first time?” The answer to that is, yes, I did say everything I had to say at the time, and the first edition is pretty comprehensive as a field guide. But that was about a dozen years into what turned out to be a 20-year journey, and after we sold Return Path in 2019, I had time to reflect on all that happened. I learned a lot of new lessons between the first and second editions, we had a lot of first-time experiences, we scaled the company significantly, and we sold it. None of those things are, in and of themselves, worthy of a second edition, but collectively they help tell the story of startup to exit and tell it from a perspective of creating a sustainable business over nearly two decades. 

But there are other reasons, too, besides new lessons learned. Eight years is a lifetime in terms of changes to micro-trends, language, business in general, and the world around us. I wanted to update the book to make it contemporary so that it can speak to a new generation of CEOs. The second edition is more than a new cover and obvious updates on the number of employees or revenues. I added topics that reflect heightened responsibilities of CEOs around moral and ethical leadership in an increasingly transparent and socially conscious world. How do you navigate a politically charged and divisive society? For example, the State of Indiana passed a law intended to not force people to do things that contravened their religious beliefs but it had the side effect of legal descrimination against LGBT citizens. It was contentious, with rallying cries in business and society for one side or the other, and those same sentiments were found within our employee population. 

How should CEOs handle a situation that conflicts with their core values? There are no easy answers, but avoiding them doesn’t make the problem go away. 

Whether it’s the #metoo movement, high-profile failures of leadership like airline employees dragging customers off of planes, or something as simple as unconscious bias in the workplace, the best CEOs now need to approach their jobs differently. I didn’t write about that in the first edition, but the second edition has an entire chapter devoted to “Authentic Leadership” and provides guidelines and advice to help CEOs. The book went to press early in the COVID-19 pandemic and prior to all the protests around racial injustice surrounding the George Floyd killing, so nothing in it specifically addresses any of those issues.  In some ways, though, that may be better at the moment since the book is more about frameworks and principles than about specific responses to current events.

I also added a new section with several chapters on the ins and outs of selling a business. Startup exits are the important culmination of the startup experience and something that the first edition only briefly touched on. Obviously, I was still CEO of a growing company and although we had an opportunity or two to sell within those first years, we never pulled the trigger. The first edition talks about that process at a surface level, but the second edition has far more content and detail since we had completed a sale transaction. 

The first edition of the book has sold close to 40,000 copies as of the writing of the second edition, which blew me away when I tallied it all up. I’ve received many notes of thanks from readers all over the world for the book, and I’m glad that the content has proved useful to so many people, noting from some of the more critical reviews on Amazon that it certainly doesn’t scratch everyone’s itch. I hope the changes in the new edition add even more value to the lives of entrepreneurs and startup management teams. That’s really who the book is written for.

Here are some places to go to pre-order the book:

• Directly from the publisher, Wiley
• From Amazon
• From Books-a-Million
• From Indie Bound 
• From BN.com

I have a limited number of free copies of the book that I can send out, and oddly, they are only print copies since the book publishing ecosystem hasn’t figured out an efficient way for authors to distribute free Kindle copies of books yet.  As a bonus incentive for reading all the way to the end of this post, I will be happy to send a free copy to the first 5 people who comment on this post on the blog and ask for one.

As I mentioned the other day, the second edition of Startup CEO is out.  This post is a teaser for the content in one of the new chapters in this edition on Authentic Leadership.

As I mentioned last week, the book went to press early in the COVID-19 pandemic and prior to all the protests around racial injustice surrounding the George Floyd killing, so nothing in it specifically addresses any of those issues.  In some ways, though, that may be better at the moment since the book is more about frameworks and principles than about specific responses to current events. Two of those principles, which are timeless and transcend turmoil, uncertainty, time and place, are creating space to think and reflect and being intentional in your actions. In a world in which CEOs are increasingly called upon to deal with more than traditional business (pricing, strategy, go-to market approaches, team building, etc.) it’s imperative to approach and solve challenging situations from a foundation that doesn’t waver. 

At Return Path our values were the foundation that provided a lens through which we made every decision. Well, not every decision, only the good ones. When we strayed from our core values, that got us into trouble. The other principle, outlined in Chapter 1 of the Second Edition, is leading an organization authentically.

Let me provide a couple concrete examples of what I mean by “Authentic Leadership” since the term can be interpreted many ways.

One example is to avoid what I call the “Say-Do” gap.  This is obviously a very different thread than talking about how the company relates to the outside world and current events.  But in some ways, it’s even more important.  A leader can’t truly be trusted and followed by their team without being very cognizant of, and hopefully avoiding close to 100%, any gap between the things they say or policies they create, and the things they do.  There is no faster way to generate muscle-pulling eyerolls on your team than to create a policy or a value and promptly not follow it. 

I’ll give you an example that just drove me nuts early in my career here, though there are others in the book.  I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a taxi home if you work past 8 pm unless it’s summer when it’s still light out at 8 pm” (or something like that).  Anyway, the policy stipulated a max an employee could spend on a hotel for a business trip, but the CEO  (who was an employee) didn’t follow that policy 100% of the time.  When called out on it, did the CEO apologize and say they would follow the policy just like everyone else? No, the CEO changed the policy in the employee handbook so that it read “blah blah blah, other than the CEO, President, or CFO, who may spend a higher dollar amount at his discretion.”

What does that say about the CEO? How engaged are employees likely to be, how much effort are they willing to devote to the company if there are special rules for the executives? You can make any rule you want — as you probably know if you have read a bunch of my posts or my book over the years, I’m a proponent of rule-light environments — but you can’t make rules for everyone else that you aren’t willing to follow yourself unless you own the whole company and don’t care what anyone thinks about you or says about you behind your back.

Beyond avoiding the Say-Do Gap, this new chapter of the book on Authentic Leadership also talks about how CEOs respond to current events in today’s increasingly politicized and polarized world.  This has always felt to me like a losing proposition for most CEOs, which I talk about quite a bit in the book.  When the world is polarized, whatever you do as CEO, whatever position you take on things, is bound to upset, alienate, or infuriate some nontrivial percentage of your workforce.  I even give some examples in the book of how I focused on using the company’s best interests and the company’s values as guideposts for reacting (or not reacting) to politically divisive or charged issues like guns or “religious liberty” laws.  I say this noting that there are some people who *believe* that their side of an issue like this is right, and the other side is wrong, but the issues have some element of nuance to them.

Today’s world feels a bit different, and I’m not sure what I would be doing if I was leading a known, scaled enterprise at this stage in the game.  The largely peaceful protests around all aspects of racial injustice in America in the wake of the murder of George Floyd — and the brutality and senselessness of that murder itself — have caused a tidal wave of dialog reaching all corners of the country and the world.  The root of this issue doesn’t feel to me like one that has a lot of nuance or a second side to the argument.  After all, what reasonable person is out there arguing that George Floyd’s death was called for, or even that black Americans don’t have a deep-seeded and widespread reasonable claim to inequality…even if their view of what to do about it differs?

I *think* what I would be doing in a broader leadership role today is figuring out what my organization could be doing to help reduce or eliminate structural racial inequality where we could based on our business, as opposed to driving my organization to take a specific political stand. I know for sure that I wouldn’t solicit feedback from a select group of people only, but I would create a space where voices from across the organization (and stakeholders outside of it as well) could be heard. That’s not a solution, but a start, and in challenging times making a little bit of headway can lead to a cascading effect. It can, if you keep the momentum.

And, in line with “authentic leadership,” it’s okay to admit that you don’t have the answers, that you might not even know the questions to ask. But doing nothing, or operating in a “business as usual” way won’t make your company stronger, won’t open up new opportunities, won’t generate new ideas, and won’t sit well with your employees, who are very much thinking about these issues. 

So, in today’s challenging times I would follow my own advice, be thoughtful and reflective, and intentional in searching for common solutions.  I’d try to avoid “mob mentality” pressure — but I would also be listening carefully to my stakeholders and to my own conscience.

In the coming weeks, I’ll write posts that get into some of the other topics I cover in the book, but none of them will be as good as reading the full thing!

As part of the new section on Exits in the Second Edition of the book (order here), there’s a specific chapter around handling the post-sale transition and integration process.  

No two transitions are exactly the same.  If the buyer is a financial sponsor, you may have the same job the day after the deal closes that you had the day before, just with a new owner and new rules for you.  Sometimes you’ll stay on with a strategic buyer as the head of a division, or the head of your product.  Sometimes you leave on Day 1.  Sometimes you leave later.  

But the most important thing you can do is remember that once the deal is over, it’s over.  That’s why an honest answer to the question, “Are you ready to let go?” that I posed in an early post is so important. You may or may not be the CEO, but now you definitely have a new boss, and in many cases, a boss for the first time in years. And you are no longer in charge.

“Even though the deal was called a merger,” I once heard Ted Leonsis tell the Moviefone founders a while after AOL acquired Moviefone, “please remember that you have been acquired.” Your job is to figure out how best to set your team and products up for success in the new environment, regardless of how long or short you plan to stay at the new company. 

We tried to focus our transition at Return Path to Validity in a few ways:

• For employees, we spent most of our energy and our capital setting things up in the deal documents before closing, recognizing we’d have no control of things after the deal was signed.  Things like how much severance people would get if they were let go, and for how long post-deal, how much their comp could change, whether they could be required to move – those are all things you can negotiate into a deal
• For ourselves as leaders and me as CEO, knowing most of us would leave almost immediately post-deal, I wanted to have as elegant an exit as possible after 20 years.  Fortunately, I had a good partner in this dialog in Mark Briggs, the acquiring CEO.  Mark and I worked out rules of engagement and expenses associated with “the baton pass,” as we called it, that let our execs have the opportunity to say a proper goodbye and thank you to our teams, with a series of in-person events and a final RP gift pack.  This was a really important way we all got closure on this chapter in our lives
• For the new owners of the business, our objective was to be of service to them, knowing they’d want to run it differently.  So, for example, every time our new owners from Validity asked me a question (“Should we do X or Y,” or “Should we keep person A or person B?”), my answer was never simple. It was always, “What’s your strategy with regard to Z?” and then my advice could be in context, as opposed to thinking about what I would do in the prior context.

There are more details on this in the new section on exits in Startup CEO:  A Field Guide to Scaling Up Your Business.

(This post also appeared on Bolster.com)

As we wrote in our Founding Manifesto, Bolster was started in part to create a new way for startup and scaleup CEOs to think about growing their leadership teams.

Why do CEOs need help with this?

CEOs of any company have too many things to do at all times. This is even more true at startups and scaleups, which by definition are more fast-paced, dynamic, CEO-driven, and thinly staffed. All those challenges point directly to the specific challenge CEOs have with their leadership team.

Think about the journey of a company from a founding team to 50 employees. My long time friend and former board member Greg Sands once compared the phenomenon

of companies growing out of the startup stage to cell development in small organisms. Amoeba or paramecia consist of one cell, and that cell has to do everything: eat, move, sense its surroundings, and respond accordingly. When the cell divides, the new cells still need to do everything – they’re just attached to other cells. As organisms grow more complex, individual cells need to specialize. And when things get really complex, you need a liver, a spleen, a stomach, and a pancreas. By and large, startups work the same way. In the early stages, you have to hire generalists who are both willing and able to take on dozens of tasks at once. Your developers will have to speak with potential customers; your accountants will have to give advice on product direction; and the born salesperson on your team will need to put the phone down a few hours a day and set up a new employee’s computer. That’s a really different team than when you need functional managers on top of engineering, sales, etc. — not to mention needing strategic leadership of those functions as the company grows from 50 to 100 to 250 to 500 employees.

That’s the journey that startup and scaleup CEOs are on. It’s less of a journey and more of a roller coaster ride. Jason is running HR today…but tomorrow, the job of “head of HR” will be different, and Jason might or might not be capable of it. Then your VP Finance Sally gets lured away by an even hotter and sexier new startup and leaves a sudden, gaping hole on your team. Then cracks start to show up with the job Jamie is doing as your marketing director and you lose confidence that your upcoming product launch is going to be a success. Every time one of these events happens – whether it’s an actual event, or just an “aha moment” for you as CEO, you add something to your plate. You add tasks to take over work yourself. You add the task of finding a new person. You add stress from having to deal with one more critical thing.

Leveling up a leadership team is probably the hardest part of the CEO’s job. 

Why don’t current solutions meet the CEO’s needs? Well, of course they do, sometimes. The problem is that the current solutions either aren’t tailored to the needs of startup or scaleup CEOs, or they’re ad hoc and inefficient. Executive search is slow and expensive, and it produces expensive full-time executives. And no matter how good an executive search firm is, I’ve never met a CEO who has a better than 50% success rate in hiring new leaders from the outside. Ever. Add all that up – expensive, slow, medium success rate, and perhaps most important for a startup CEO, leaving you with expensive full-time headcount in multiple areas of your company – that is not a recipe for startup success when you’re sweating your burn rate.

Frequently, the CEO just taps her network for execs or for on-demand executives like the ones Bolster places — that could be asking board members or friends or advisors for suggestions. Quite frankly, those suggestions stand a better chance of success than transactional executive search since the candidate referral source is usually somewhat of an insider. But those searches are really disorganized or one-off. When a CEO turns to their network for spot help, they often aren’t running a comprehensive process, creating a serious job spec, seeing a broad set of candidates for comparisons, and the like. 

Our job at Bolster is to make all of this easier and lighter weight. The rise of the gig economy means that startups no longer need to rely on the painful binary choice of “the person/opening I have today” and “the expensive full-time exec coming in from the outside.”The new way to scale an executive team is with a mix of interim executive talent to quickly fill gaps, fractional executive talent to provide strategic oversight and guidance to a team, part-time, functional mentors/coaches/advisors to advise a less experienced functional leader, project-based consultants to fill in specific holes, and yes, the occasional full-time outside hire, possibly via a search firm (or if your fractional CXO loves your company and joins full-time!). 

With Bolster, you have a network of all those types of talent, well curated and well profiled, available for near-instant matches and near-instant start dates – and a suite of tools and services designed to help you proactively identify your needs across all your functional areas so you’re never scrambling your way out of a tight spot.

What about the existing team? If you’re a leader inside a startup or scaleup, Bolster is ALSO created for you. The painful binary choice CEOs face that I wrote above is particularly painful for you if you’re no longer scaling quickly enough. Frequently, promising junior people are layered or shuttered aside because the CEO doesn’t have the time, or the functional expertise required, to coach or mentor the person to success. Bolster creates an easy mechanism for CEOs to help pinpoint the areas in which you need growth and development as well as an easy way to find either temporary leadership or a function-specific advisor/mentor/coach to help you grow with the role and with the company.

The best startup CEOs I know are the ones who are already using multiple types of on-demand talent at the same time to help their companies along that journey from single-cell to complex organisms. I believe three years from today, the frequent usage of this kind of talent will move from the realm of early adopters to mainstream. The ones who embrace it first will have a competitive advantage.

(Written by both my Bolster co-founder Cathy Hawley and me)

I’ve attended two remote conferences, which Cathy dubbed “Zoomsites” — one here at Bolster and the Foundry Group CEO Summit.  Both hold interesting lessons for how these kinds of events can work well.

We founded Bolster two months into the COVID-19 pandemic, and our founding team had not met in person after 6 months of working together. Now, luckily, we’ve all worked together for many years, so we have a lot of trust built up, and have a very strong operating system which includes full team daily standups. Still, nothing beats face-to-face interaction. If you’ve ever founded a startup, you know how impactful it can be to work side by side, bounce ideas off each other, and collaborate as you learn more about opportunities and challenges in your market. 

We also have a strong belief in the power of the team, and the need to work together to ensure that we are aligned on all aspects of the business. And, we had a successful launch, with more interest in our marketplace than we had anticipated, so we knew we needed to step back to have a planning and strategy session.

We’ve done many executive offsites, and couldn’t imagine having an impactful offsite remotely, and we all agreed that we would be comfortable meeting up in person. So we started planning a 2-day offsite together in New York. Unfortunately, it turned out visitors to NY from Colorado and Indiana, the two states we were traveling from, needed to quarantine for 10 days when they got to NY. While technically we could get around this because we weren’t staying for 10 days, we decided to follow the spirit of the rules, and cancel our travel.

Since we really needed to have the planning and strategy session, and we’d blocked the two full days on our calendars, we decided to test out a ‘zoomsite’ – an all-remote video call. We modified the agenda a little – some things good in person fall flat on video. We knew we wanted to have really engaging conversations, and keep the agenda moving along, so that all eight of us could fully participate and complete the necessary work. I’m happy to say that we came out of the offsite with a revised strategic plan, new six-month goals set, and owners for each of the different workstreams. And, we had fun. Success!

The Foundry Group CEO Summit has been a different animal — it’s wrapping up today, but there’s been enough of it so far this week to comment on.  Foundry took a regular annual event with a large group (50-75) and moved it online.  They did a great job of adapting to the medium, spreading the event out with a few hours a day over multiple days to avoid Zoom fatigue and optimize attendance; scheduling content in shorter bursts than usual; making good use of breakout room technology; and encouraging heavy use of Zoom’s chat feature during sessions to make it as interactive as possible.  Like the Bolster event, there were some elements missing — all the great “hallway conversations” you have at in-person conferences where people are staying in the same hotel and seeing each other at meals, in the gym, between sessions, etc.  But it has also been a big success with enough community elements to make it worthwhile. 

Want to have a Zoomsite? Here are some tips:

• Make sure you have the tools needed for each activity. When you are brainstorming in person, you may use sticky notes or flip charts to write on. Remotely, you can use Google Docs or Sheets or tools like Note.ly or Miro
• Prep the sheets or docs ahead of time, so that people can engage in the activities easily. At our Zoomsite, we modified our blue-sky brainstorm session so that we each answered a few questions in a Google Sheet. We had a separate section for each person, and the exercise was easy to understand and engage in, and people got straight to work.
• Schedule in more breaks, shorter sessions, or less than full-day meetings. We had a couple of hour-long breaks during the day, which helped people to focus.  Foundry did a great job of getting everyone’s attention for a few hours every day, for more days than a normal in-person conference
• Plan your technology. At the Bolster meeting, we learned this the hard way. We tested out the idea of doing a “walk and talk” session where we’d each walk in our neighborhoods, and have a couple of strategic conversations just on the phone. Unfortunately, the technology didn’t work for everyone, as they hadn’t all used Zoom on their phones before, it was windy in some locations, and cell service dropped people from time to time.  Probably not the best idea we had!
• Include a social component. We were a little skeptical about this at the Bolster Zoomsite, but we’d always incorporated social time into offsites, and we really value connecting as people, not just as professionals, so we gave it a try. On the second day of our Zoomsite, we took a 2 hour break at the end of the day, and came back for drinks and dinner together. We had personal conversations, including sharing our favorite tv shows. Eight people on video eating together might sound odd, and we weren’t sure if it would work, but we all agreed that it was fun, and we’d do it again.  I missed the Foundry “Virtual Fun” session, but they did a virtual game show run by our sister portfolio company, Two-Bit Circus (and also had investigated Jack Box Games as another option for virtual games via Zoom screen share plus real-time voting and other engagement via phone).  I heard that session was great and engaging from people who attended

We all hope life returns to some kind of normal in 2021, though it’s unclear when that will be.  And there’s definitely value to doing meetings like this in person, but at least we now know that we can have a successful remote offsite or larger conference event.  As with everything, it will be interesting to see how the world is changed by COVID.  Maybe events like this will figure out how to mix remote and in-person participation, or alternate between event formats to keep travel costs down.

Post 4 of 4 in the series of Scaling CMO’s- the other posts are, When to Hire your First Chief Customer Officer, What does Great Look like in a Chief Customer Officer and Signs your Chief Customer Officer isn’t Scaling.

You can engage with each person on the executive team one-on-one to understand what their issues and challenges are, but I’ve found that engaging with the CCO offsite with customers is far more productive and leads to a better understanding of the service organization than any other meeting time. I have typically spent the most time with or gotten the most value out of CCOs over the years doing the following.

In person at “Canary in the Coal Mine” customers. They don’t use canaries any more in coal mines, but the principle applies to companies: What are the early warning signs that you’ve got big problems looming? The earlier you discover those problems the better, and the CCO is usually the first person to figure out that something isn’t right with your product or service. I always find that the largest clients, the most demanding ones, the ones who push you around, the ones who are highly critical or you, are the ones who make your company a better company.  At Return Path, we had those types of clients over the years, from eBay, to DoubleClick, to Microsoft, to Groupon, to Facebook, to Bank of America—and that’s just the short list off the top of my mind.  The demanding customer is the one who breaks things and forces you to own up to your lack of scalability.  They also either take you to task or threaten to pull their business if you don’t clean up your act.  As painful as some of those meetings are, they are also ones I always wanted to attend in person with my CCO, both so I could eat whatever form of crow needed to be eaten as the Chief Crow Eater (which sends a very powerful message to the customer), and also because the CCO and I could experience the chirping of the canary in the coal mine and learn from the experience together.

While it’s important to engage with the CCO in the critical meetings with demanding customers, it’s also important to understand the base.  There’s an old saying from the hardware world that goes, “God was able to create the world in only 7 days because God didn’t have an installed base.”  The new world of Internet technologies, SaaS, and agile development is one where your installed base of customers is your biggest asset, not a millstone around your neck.  Some of the most meaningful experiences I had over the years with our CCOs was to be in market, spending time with all kinds of customers together in small groups and large, deeply understanding their needs and use of our product.

The CCO role is one that is easy to ignore or put on the back burner if things are going smoothly at your company, but as CEO I feel that it is best to stay close to the market and engaging with the CCO with demanding customers and with the base is a good way to understand your company and CCO better.

(You can find this post on the Bolster Blog here)