(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…

I’ve said this for years, but as I sit on the train commuting into work after a week off relaxing with my family for my Dad’s 75th birthday (or as he prefers to call it, the 46th anniversary of his 29th birthday), I feel particularly inclined to write it up!

I love my job, so I almost never mind going to work. But I also love being on vacation and traveling with my family and try to do as much of it as I can. Years ago before we had kids and became tethered to school and sports schedules, we used to take at least one full two week vacation, completely unplugged, at least once a year. I miss that!

The problem with any vacation longer than a couple days off (which is NOT a vacation) is that it can take several days to unwind, decompress from work and the small stresses of every day life, and unplug, meaning not checking email, reading blogs or the newspaper every morning, and not fidgeting every time you’re more than 10 feet away from your smartphone. Then on the other end of the trip, trying to triage email the day before you go back to work and generally gearing up for reentry into the fast lane also consume a bunch of cycles — and for me, I’ve never been able to sleep well the night before the first day of anything, so it means starting back with diminished relaxation even before walking through the office door.

So all in, that means the true part of a week-long, meaning 9-day vacation (including two weekends), is about 4-5 days.

That’s not bad. But I think you have all that same overhead associated with a two week vacation as well…so a two week vacation of 16 days leaves you with 11-12 days. Mathematically, if not psychically, more than twice as good as the standard one-weeker.

I’m inclined to start doing that once a year again, schedules be damned!

As a side note, two things I also used to do on vacation, even a one-weeker, that I am regretting not doing this time are (a) actually turning my work email account off my phone and leaving it off until the Monday morning after vacation so there’s no cheating on a couple minutes of email here or there, and (b) making sure my schedule is almost completely open that first Monday back to catch up. Next time, those two features will return prominently…along with that full second week off.

Oh, and if anyone says a Startup CEO can’t take a long unplugged vacation…I call bullshit. You may not be able to do it any two weeks of the year with no notice, but plan ahead, leave things in good order, leave someone in charge (or don’t, but be deliberate about that), and let them know where to call you in case the building burns down. It will be fine when you get back, and healthy for tour team to have a break from you as well.

Book Short:  Like Reading a Good Speech

Leaders Eat Last, by Simon Sinek, is a self-described “polemic” that reads like some of the author’s famous TED talks and other speeches in that it’s punchy, full of interesting stories, has some attempted basis in scientific fact like Gladwell, and wanders around a bit.  That said, I enjoyed the book, and it hit on a number of themes in which I am a big believer – and it extended and shaped my view on a couple of them.

Sinek’s central concept in the book is the Circle of Safety, which is his way of saying that when people feel safe, they are at their best and healthiest.  Applied to workplaces, this isn’t far off from Lencioni’s concept of the trust foundational layer in his outstanding book, Five Dysfunctions of a Team.  His stories and examples about the kinds of things that create a Circle of Safety at work (and the kinds of things that destroy them) were very poignant.  Some of his points about how leaders set the tone and “eat last,” both literally and figuratively, are solid.  But his most interesting vignettes are the ones about how spending time face-to-face in person with people as opposed to virtually are incredibly important aspects of creating trust and bringing humanity to leadership.

My favorite one-liner from the book, which builds on the above point and extends it to a corporate philosophy of people first, customer second, shareholders third (which I have espoused at Return Path for almost 15 years now) is

Customers will never love a company unless employees love it first.

A couple of Sinek’s speeches that are worth watching are the one based on this book, also called Leaders Eat Last, and a much shorter one called How Great Leaders Inspire Action.

Bottom line:  this is a rambly book, but the nuggets of wisdom in it are probably worth the exercise of having to find them and figure out how to connect them (or not connect them).

Thanks to my fellow NYC CEO Seth Besmertnik for giving me this book as well as the links to Sinek’s speeches.

What Kind of Entrepreneur Do You Want to Be?

I had a great time at Princeton reunions this weekend, as always.  As I was talking to random people, some of whom I knew but hadn’t seen in a long time, and others of whom I was just meeting for the first time, the topic of starting a business naturally came up.  Two of the people asked me if I thought they should start a business, and what kind of person made for a good entrepreneur.

As I was thinking about the question, it reminded me of something Fred once told me — that he thought there were two kinds of entrepreneurs:  people who start businesses and people who run business. 

People who start businesses are more commonly known as serial entrepreneurs.  These people come up with ideas and love incubating them but may or may not try to run them longer term.  They:

– generate an idea a minute
– have a major case of ADD
– are easily distracted by shiny objects
– would rather generate 1 good and idea and 19 bad ones than just 1 good one
– are always thinking about the next thing
– are only excited by the possibility of what could be, not what is
– are more philosophical and theoretical
– probably shouldn’t run the companies they start for more than a few months, as they will frustrate everyone around them and get bored themselves
– are really fun at cocktail parties
– say things like “I thought of auctions online way before eBay!”

The second type of entrepreneur is the type who runs businesses (and may or may not come up with the original idea).  These people:

– care about success, not just having the idea
– love to make things work
– would rather generate 1 idea and execute it well than 2 ideas
– are problem solvers
– are great with people
– are maybe less fun at cocktail parties, but
– you’d definitely want them on your team in a game of paintball or laser tag

Neither one is better than the other, and sometimes you get both in the same person, but not all that often.  But understanding what type of entrepreneur you are (or would likely be) is probably a good first step in understanding whether or not you want to take the plunge, and if so, what role you’d like to play in the business.

A New VC Ready to Go!

One of the interesting things about being in business for 13 years (as of last week!) at Return Path is that we have been around longer than two of our Venture Capital funds.  Fortunately for us, Fred led an investment in the company with his new fund, Union Square Ventures, even though his initial investment was via his first fund, Flatiron Partners.  And even though Brad hasn’t invested out of his new fund, Foundry Group, he remains a really active member of our group as a Board Advisory through his Mobius Venture Capital investment.

Although our third and largest VC shareholder, Sutter Hill Ventures, is very much still in business, our Board member Greg Sands just announced today that he has left Sutter and started his own firm, Costanoa Venture Capital, sponsored in part by Sutter.  The firm was able to buy portions of some of Greg’s portfolio companies from Sutter as part of its founding capital commitment, so Return Path is now part of both funds, and Greg, like Fred, will continue to serve as a director for us and manage both firms’ stakes in Return Path.

The descriptions of the firm in Greg’s first blog post are great – and they point to companies like Return Path being in his sweet spot:  cloud-based services solving real world problems for businesses, Applied Big Data, consumer interfaces and distribution strategies for Enterprise companies.

I give Greg a lot of credit for going out on his own with a strong vision, something that’s unusual in the VC world.  We’re proud to be part of his new portfolio, and I’m sure he’ll be incredibly successful.  Like Fred and Brad and their new firms, Greg understands the value of being able to write smaller initial checks and back them up over time, he is a disciplined investor, and he is a fantastic Board member and mentor.

Selecting Your Investors

Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures.  We’ve been through a lot of wars together.  In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class.  This is the first one…and Fred’s post on the other side of the topic is here.  Next week, we’ll address the topic of building a successful CEO-VC partnership once it’s established.

If you’re fortunate enough to have built a really strong early stage company, you will find yourself in the position of being able to pick from a number of potential venture investors.  The better your business and the more exciting the space you’re trying to tackle…the more investors you’ll find circling around you.  Here are a few tips for ending up with the best long-term partner as an investor.

1. Look for VC portfolios that have a lot of “like” companies (B2B, B2C, media, tech, etc.).  One of the strongest points of value that venture investors bring to the table is pattern matching, and you can maximize that by making sure the investor you end up with has seen a multitude of companies like yours
2. Check references carefully.  Don’t be shy – prospective VCs are checking up on you, and you have every right to do the same with them.  When Fred first invested in Return Path, he gave me a list of every CEO he had ever worked with and said “Call anyone you want on the list.  Some of these guys I worked well with, a couple I fired.  But they’ll all tell you what I’m like to work with.”  First prize is the VC who volunteers this information.  Second prize is the VC who gives it to you when you ask.  A distant third price is the VC who gives you two names and ask for time to prep them ahead of time
3. Focus on the person first, the firm second.  Having a good venture firm is important.  But at the end of the day, you’re dealing with a person first and foremost.  That’s who will be on your board giving you advice and measuring your performance.  Better to have an A person at a B firm than a B person at an A firm (of course, even better to have an A person at an A firm).  This means two things – selecting a great person to be on your Board, and also making sure you end up with a person who has enough juice within his or her firm to get things done on your behalf with the partnership
4. Always have a BATNA (Best Alternative to a Negotiated Agreement – a fancy way of saying Plan B).  This is probably the most important piece of advice I can offer.  And this is true of any negotiation, not just a term sheet.  It’s often said that good choices come from good options. Sometimes, you have to walk away from a deal where you’ve invested a lot of time, energy, and emotion.  But as an entrepreneur, you can mitigate the number of times you have to walk away by developing good alternative options to a particular deal. That way, if one option doesn’t pan out as you’d hoped, another very good option is waiting in the wings.  If you negotiate with two or three VCs, you’ll have a great backstop and won’t let the emotional investment in the deal get the best of you.  Yes, you will spend twice to three times the amount of time on the process, but it’s well worth it
5. Don’t be swayed by promises of help.  I’ve heard VCs say it all.  They’ll help you fill out your management team.  They’ll get you customers.  They’ll help with your back office.  They’re loaded up with value-add.  If venture investor has staffed his or her firm with support personnel who are available free of charge to portfolio companies (this does happen once in a while), then assume your VC will be as helpful as possible, but no more or less helpful than another investor
6. Handle the negotiation yourself, in person as much as possible.  The best way to get to know someone’s character is to negotiate a deal with him.  This gives you lots of opportunities to look for reasonableness, and to see if he or she is able to focus on the big picture.  The biggest warning sign to look for is someone who says things like “you have to agree on this term, because this is how we always do deals.”  By the way, how you handle yourself in this negotiation is equally important.  The financing is the line of demarcation between you and the VC courting each other, and the VC joining your board and effectively becoming your boss
7. “Pay up” for quality and for a clean security.  There is a world of difference between good VCs and bad VCs (both the individual partners and the firms) that will ultimately have a lot to do with how successful your company can become.  The quality of your VC isn’t more important than the quality of your product or your team, but it’s right up there.  But – and this is an important but – you should expect to “pay” for quality in the form of slightly weaker terms (whether valuation or type of security).  Similarly, I’d always sacrifice valuation for a clean security.  Everyone always thinks that price/valuation is the most important thing to maximize in a deal. However, the structure of the security can be much more important in the long run.  Whether the VCs buy 33 percent of your company or 30 percent of your company is much less important than having a capital structure that’s easy for an outsider to understand and want to join

As with all things, there are probably another dozen items that could be added to this list, but it’s a good starting point.  However, your more important role as CEO is to put your company in a position where you can select from a number of high quality investors, so start there!

(Excerpted from Chapter 12 of Startup CEO)

As a CEO, one of the most important things you can do is solicit feedback about your own performance. Of course, this will work only if you’re ready to receive that feedback! What does that mean? It means you need to be really, really good at doing four things:

1. Asking for feedback
2. Accepting feedback gracefully
3. Acting on feedback
4. Asking for follow‐up feedback on the same topic to see how you did

In some respects, asking for it is the easy part, although it may be unnatural. You’re the boss, right? Why do you need feedback? The reality is that all of us can always benefit from feedback. That’s particularly true if you’re a first‐time CEO. Even more experienced CEOs change over time and with changing circumstances. Understanding how the board and your team experience your behavior and performance is one of the only ways to improve over time. It’s easier to ask for feedback if you’re specific. I routinely solicit feedback in the major areas of my job (which mirror the structure of this book):

Strategy. Do you think we’re on target with what we’re doing? Am I doing a good enough job managing to our goals while also being nimble enough to respond to the market?

Staff management/leadership. How effective am I at building and maintaining a strong, focused, cohesive team? Do I have the right people in the right roles at the senior staff level?

Resource allocation. Do I do a good enough job balancing among competing priorities internally? Are costs adequately managed?

Execution. How do the team and I execute versus our plans? What do you think I could be doing to make sure the organization executes better?

Board management/investor relations. Do you think our board is effective and engaged? Have I played enough of a role in leading the group? Do you as a director feel like you’re contributing all you can? Do I strike the right balance between asking and telling? Are communications clear enough and regular enough?

Accepting feedback gracefully is even harder than the asking part. You may or may not agree with a given piece of feedback, but the ability to hear it and take it in without being defensive is the only way to make sure that the feedback keeps coming. Sitting with your arms crossed and being argumentative sends the message that you’re right, they’re wrong, and you’re not interested. If you disagree with something that’s being said, ask questions. Get specifics. Understand the impact of your actions rather than explaining your intent.

The same logic applies to internalizing and acting on the feedback. If you fail to act on feedback, people will stop giving it to you. Needless to say, you won’t improve as a CEO. Fundamentally, why ask for it if you’re not going to use it? And that leads right into the fourth point, closing the loop with the person who gave you feedback on whether or not your actions achieved the desired change.

My father-in-law, who is a doctor by training but now a health care executive, was recently talking about an unusual medical condition that someone in the family was fighting.  He had a wonderful expression he said docs use from time to time:

When you hear hoof beats, it’s probably horses. But you never know when it might be a zebra.

With experience (and presumably some mental wiring) comes the ability to recognize patterns.  It’s one of those things that doesn’t happen, no matter how smart you are, without the passage of time and seeing different scenarios play out in the wild.  It’s one of the big things that I’ve found that VC investors as Board members, and independent directors, bring to the Board room.  Good CEOs and senior executives will bring it to their jobs.  Good lawyers, doctors, and accountants will bring it to their professions.  If X, Y, and Z, then I am fairly certain of P, D, and Q.  Good pattern recognition allows you to make better decisions, short circuit lengthy processes, avoid mistakes, and much better understand risks.  The value of it is literally priceless.  Good pattern recognition in our business has accelerated all kinds of operational things and sparked game changing strategic thinking; it has also saved us over the years from making bad hires, making bad acquisitions, and executing poorly on everything from system implementations to process design.  Lack of pattern recognition has also cost us on a few things as well, where something seemed like a good idea but turned out not to be – but it was something no one around the Board table had any specific experience with.

But there’s a limitation, and even a downside to good pattern recognition as well.  And that is simple – pattern recognition of things in the past is not a guarantee that those same things will be true in the future.  Just because a big client’s legal or procurement team is negotiating something just like they did last time around doesn’t mean they want the same outcome this time around.  Just because you acquired a company in a new location and couldn’t manage the team remotely doesn’t mean you won’t be able to be successful doing that with another company.

The area where I worry the most about pattern recognition producing flawed results is in the area of hiring.  Unconscious bias is hard to fight, and stripping out markers that trigger unconscious bias is something everyone should try to do when interviewing/hiring – our People team is very focused on this and does a great job steering all of us around it.  But if you’re good at pattern recognition, it can cause a level of confidence that can trigger unconscious biases.  “The last person I hired out of XYZ company was terrible, so I’m inclined not to hire the next person who worked there.”  “Every time we promote someone from front-line sales into sales management, it doesn’t work out.”  You get the idea.

Because when you hear hoof beats, it’s probably horses.  But you never know when it might be a zebra!

Boards That Lead, by Ram Charan, Dennis Carey, and Michael Useem, was recommended to me by a CEO Coach in the Bolster network, Tim Porthouse, who said he’s been referring it to his clients alongside Startup Boards. I don’t exactly belong in the company of Ram Charan (Brad and Mahendra probably do!), so I was excited to read it. While it’s definitely the “big company” version to Startup Boards, there are some good lessons for startup CEOs and founder to take away from it.

The best part about the book as it relates to ALL boards is the framework of Partner, Take Charge, Stay out of the Way, and Monitor. You can probably lump all potential board activities into these four buckets. If you look at it that way…these are pretty logical:

• Monitor – what you’d expect any board to do
• Stay out of the Way – basic execution/operations
• Partner – strategy, goals, risk, budget, leadership talent development
• Take Charge – CEO hiring/firing, Exec compensation, Ethics, and Board Governance itself.

There was an interesting nugget in the book as well called the Central Idea that I hadn’t seen articulated quite this way before. It’s basically a statement of what the business is and how it’s going to win. It’s about a page long, 8-10 bullet points, and it includes things like mission, strategy, key goals, and key operating pillars that underlie the goals. It basically wraps up all of Lencioni’s key questions in one page with a little more meat on the bones. I like it and may adopt it. The authors put the creation of the Central Idea into the Take Charge bucket, but I’d put it squarely in the Partner bucket.

Other than that, the book is what you’d expect and does have a lot of overlap with the world of startups. Its criteria for director selection are very similar to what we use at Bolster, as is its director evaluation framework. The book has a ton of handy checklists as well, some of which are more applicable than others to startups, for example Dealing with Nonperforming Directors and Spotting a Failing CEO.

All in, a good read if you’re a student of Boards.

Scaling the Team

(This post was requested by my long-time Board member Fred Wilson and is also running concurrently on his blog today.  I’ll be back with the third and fourth installments of “The Best Laid Plans” next Thursday and the following Thursday)

When Return Path reached 100 employees a few years back, I had a dinner with my Board one night at which they basically told me, “Management teams never scale intact as you grow the business.  Someone always breaks.”  I’m sure they were right based on their own experience; I, of course, took this as a challenge.  And ever since then, my senior management team and I have become obsessed with scaling ourselves as managers.  So far, so good.  We are over 300 employees now and rapidly headed to 400 in the coming year, and the core senior management team is still in place and doing well.  Below are five reasons why that’s the case.

1. We appreciate the criticality of excellent management and recognize that it is a completely different skill set from everything else we have learned in our careers.  This is like Step 1 in a typical “12-step program.”  First, admit you have a problem.  If you put together (a) management is important, (b) management is a different skill set, and (c) you might not be great at it, with the standard (d) you are an overachiever who likes to excel in everything, then you are setting the stage for yourself to learn and work hard at improving at management as a practice, which is the next item on the list.
2. We consistently work at improving our management skills.  We have a strong culture of 360 feedback, development plans, coaching, and post mortems on major incidents, both as individuals and as a senior team.  Most of us have engaged on and off over the years with an executive coach, for the most part Marc Maltz from Triad Consulting.  In fact, the team holds each other accountable for individual performance against our development plans at our quarterly offsites.  But learning on the inside is only part of the process.
3. We learn from the successes and failures of others whenever possible.  My team regularly engages as individuals in rigorous external benchmarking to understand how peers at other companies – preferably ones either like us or larger – operate.  We methodically pick benchmarking candidates.  We ask for their time and get on their calendars.  We share knowledge and best practices back with them.  We pay this forward to smaller companies when they ask us for help.  And we incorporate the relevant learnings back into our own day to day work.
4. We build the strongest possible second-level management bench we can to make sure we have a broad base of leadership and management in the company that complements our own skills.  A while back I wrote about the Peter Principle, Applied to Management that it’s quite easy to accumulate mediocre managers over the years because you feel like you have to promote your top performers into roles that are viewed as higher profile, are probably higher comp – and for which they may be completely unprepared and unsuited.  Angela Baldonero, my SVP People, and I have done a lot here to ensure that we are preparing people for management and leadership roles, and pushing them as much as we push ourselves.  We have developed and executed comprehensive Management Training and Leadership Development programs in conjunction with Mark Frein at Refinery Leadership Partners.  Make no mistake about it – this is a huge investment of time and money.  But it’s well worth it.  Training someone who knows your business well and knows his job well how to be a great manager is worth 100x the expense of the training relative to having an employee blow up and needing to replace them from the outside.
5. We are hawkish about hiring in from the outside.  Sometimes you have to bolster your team, or your second-level team.  Expanding companies require more executives and managers, even if everyone on the team is scaling well.  But there are significant perils with hiring in from the outside, which I’ve written about twice with the same metaphor (sometimes I forget what I have posted in the past) – Like an Organ Transplant and Rejected by the Body.  You get the idea.  Your culture is important.  Your people are important.  New managers at any level instantly become stewards of both.  If they are failing as managers, then they need to leave.  Now.

I’m sure there are other things we do to scale ourselves as a management team – and more than that, I’m sure there are many things we could and should be doing but aren’t.  But so far, these things have been the mainstays of happily (they would agree) proving our Board wrong and remaining intact as a team as the business grows.

(This is the second in a series of three posts on this topic.)

In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you.  First, you need to find candidates.  Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this.  Those trusted sources could be your VC or independent board members, friends, fellow CEOs — or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them.

Selecting a CEO Mentor is literally like selecting a teacher but at a vocational school, not at a research university.  You want to select someone who has done something several times or for several years; done it really well; documented it in some organized way (at least mentally); and can articulate what they did, why, what worked and what didn’t, and help you apply it to your situation.  Do you want to be taught how to be an electrician by someone with a PhD in Electrical Engineering, or by someone who has been a master electrician for 20 years?   Fit matters mostly around values.  It’s hard to get advice from someone whose values are quite different, as their experiences and their metrics for what did and didn’t work won’t apply well to yours.  Fit is a lot less around personality, although you have to be able to get along and communicate with the person at a basic level  Find someone with the right experience set that you can learn from RIGHT NOW.  Or at least this year.  Maybe the person is the right mentor next year, maybe not.  Depends on what you need.  For example, if you’re running a $10mm revenue DTC company, find someone who has scaled a company in the DTC or adjacent eCommerce space to at least $25-50mm. 

Although I’ve been very international in getting mentoring as a CEO over the years, I’ve never hired a formal CEO Mentor. Several people, from my dad to my independent directors to the members of my CEO Forum have played that role for me at different times over the years. Knowing what I know now, I’m working with CEO Mentors who have experience with talent marketplaces at different scale, since this is a new industry for me.

Selecting a CEO Coach is different.  I got lucky in my selection of a CEO Coach almost 20 years ago.  My board member Fred Wilson told me I needed to work with one, I naively rolled my eyes and said ok, he introduced me to Marc Maltz, I told Marc something like “I need a coach because clearly I need to learn how to manage my Board better,” and for some reason, he decided to take the assignment.  I got lucky because Marc ended up being exactly the right coach for me, going on 20 years now, but I didn’t know that at the time.  

Selecting a CEO Coach is all about who you “click with” personality wise, and what you need in order to be pushed to grow developmentally.  CEO Coaches come on a spectrum ranging from what I would call “Quasi-Psychiatrist” on one end, to “Quasi-Management Consultant” on the other end.  The former can be incredibly helpful — just note that you will find yourself talking about your thoughts, feelings, and family of origin a fair bit as a means of uncovering problems and solutions.  The latter can be helpful as well — just note that you will find yourself talking about business strategy and having someone hold up the proverbial mirror so you can see you the way other people see you as the CEO, quite a bit.  There is no right or wrong universal answer here to what makes someone the right choice for you.  For me, if one end of the spectrum is a 1 and the other is a 5, I prefer working with people who are in the 3-4 range.  

Therapy and coaching are different, though.  A good CEO Coach who is a 1 will refer clients to therapy if they see the need. While coaching can “feel” therapeutic, and actually may be therapeutic, it is not a replacement for therapy. The differences between the 1s and the 5s are not just style differences but also really what you want the content of the coaching to be.  A 1 is going to help you discover and drive to your leadership style.  A 5 is going to help you align those decisions to how you actually act, what approaches you bring to the organization and how you address challenges.  Some CEO Coaches can move back and forth between all of these, but knowing where you sit with your needs relative to the coach’s natural style when you pick a coach is critical.

I know CEOs who have shown tremendous growth as humans and leaders with Coaches who are 1s and Coaches who are 5s.  A good CEO Coach is someone you can work with literally forever.   

I always encourage CEOs to interview multiple Coaches and specifically ask them what their coaching process is like and what their coaching philosophy is.  How do they typically start engagements.  How structured or unstructured are they in their work?  Check references and ask some of their other CEO clients what it’s been like to work with them.  This is all true to a much lesser extent with Mentors.  In both cases, you should probably do a test session or two before signing up for a longer-term engagement.  You wouldn’t buy a car without taking it for a test drive.  This is an even more consequential decision.  

And in both cases, there should be no ego in the process.  You should never feel like you’re being sold by a CEO Coach or CEO Mentor.  And they shouldn’t feel hurt by you picking someone else, either.  Alignment and chemistry are so critical – there is no way to have that with every person, and the good professionals in this industry should know that.

The bottom line is that hiring a CEO Mentor is low risk. If it’s not working out, you stop engaging. Hiring a CEO Coach is a longer-term decision, and it’s worth having couple of sessions with a coach before making the commitment.

Next post in the series coming:  How to get the most out of working with a CEO Mentor or CEO Coach