Sep 28 2022

Startup Boards:  VCs and CEOs need to do their jobs!

Was anyone else as appalled as I am by the contents of Connie Loizos’s recent article, Coming out of COVID, investors lose their taste for board meetings? The stories and quotes in the article about VCs reducing their interest and participation in Board meetings, not showing up, sending the junior associate to cover, etc. are eye opening and alarming if widespread. 

The reasons cited in the article are logical—overextended VCs, Zoom fatigue, and newbie directors. Connie’s note that “privately, VCs admit they don’t add a lot of value to boards” is pretty funny to read as a CEO who has heard a ton of VCs talk about how much value they add to boards (although the good ones DO add a lot of value!).  

For the most part, everything about the substance of this article just made me angry.  

Disengaged or dysfunctional boards aren’t just bad for CEOs and LPs; they’re bad for everyone. If the world has truly become a place where the board meeting is nothing more than a distraction for CEOs, and investors think it’s a tax they can’t afford, then it’s time to hit the reset button on boards and board meetings. 

Here are four things that need to happen in this reset:

VCs need to do their job well or stop doing it. The argument that investors did too many deals in the pandemic so now they don’t have any time is a particularly silly one, since the pandemic reduced the amount of time VCs needed to spend on individual board meetings as well. I used to have four board meetings each year with directors who were traveling for the meetings, having dinners, spending time with the team and sitting in on committee meetings. 

Today, boards are lucky to have one in-person meeting a year (more on that later). And as everything else takes less time, and there’s little transit, any given VC should have doubled the time they spend on board meetings.

Serving on a board post-investment is a central part of the VC role. They have obligations to the founders they back and to the LPs they represent. The entire role is “find deals, execute deals, manage the portfolio.” 

If they no longer have time for the third job, they need to admit that to both founders and LPs before stepping down. If a VC can’t be bothered to focus on minding their investments and adding value, they should work with the company to find their replacement.  

CEOs need to take their job as leader of the board seriously. Would a good CEO just throw their hands up if they found management team meetings boring or a waste of time? No. They’d fix the structure of the team or meetings. If not, they shouldn’t be the CEO. 

It’s no different with boards. Whether or not the CEO is the board chair, they’re the leader of the organization. So, one of the few “must do” items in their job description is leading the board. The board is part of the CEO’s team, just like the management team. 

CEOs get to call the meetings, run the meetings, and insist on attendance. The CEO’s obligation is to make it easy and meaningful for everyone so the board isn’t a tax but rather a secret weapon for the company’s success. As my long-time independent director Scott Weiss used to tell me, boards consume whatever you put in front of them. Garbage in, garbage out. That means paying careful attention to the board materials, to meeting etiquette, and everything in between.

If the CEO doesn’t know how to do that, they should find a CEO mentor who can teach them, observe some well run boards in action through their network, or read Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, a book I just published along with co-authors and VCs Brad Feld and Mahendra Ramsinghani.

Here’s one tip on making Board prep more efficient: work your Operating System and your Board Book formats so you do one set of reporting for the company and management team that is 95% reusable without any changes for your board.

The format for Board meetings needs to evolve. Board meetings need to evolve in our world of hybrid work just as office work needs to evolve. The format that works for in-person can’t just “lift and shift” to Zoom as is, indefinitely.

Here’s how I’m steering my board:

  • I insist on one or two “old school” meetings per year, meaning in-person attendance required, half a day long, and including a meal and even an activity. If I’m only going to see my directors together infrequently, I make it mandatory, but I also make it worthwhile and fun.
  • Remote meetings that happen between the in-person meetings are becoming shorter and tighter. I still send out a lot reading material beforehand, but I make sure to keep the focus on a fixed number of major topics to keep the discussion engaging.
  • We need a new set of expectations around Zoom meeting etiquette for long meetings. It’s okay to ask people to close their email, browser, and Slack before the meeting starts. If a meeting is more than two hours long, a 15 minute break in the middle is important. Use breakout rooms to mix up topic discussions and working sessions.
  • I am trying a new meeting format to maximize director conversation and team development. I start every meeting with a director-only session for half an hour that’s not exactly an Executive Session but is more fun and social—usually including a nonwork discussion topic, as if we were sitting around the dinner table having a cocktail. That gets the conversational juices flowing. Then when my team and observers join the meeting, I ask those people to turn their video off, and I ask directors to adjust their Zoom setting to “hide participants not on video” to keep the number of Zoom squares down to the bare minimum. Any time a team member or observer wants to engage in a particular topic, they turn their video on. Then we follow the meeting with Executive Session and Closed Session and a single-director debrief with me. That is a lot of moving pieces to manage, I find that but doing so keeps the meeting fresh and well paced.
  • Finally, I’m following Fred Wilson’s advice and running a very short survey post-meeting to ask directors basic questions so they can summarize their thinking for me and the team: What are we doing well? What do we need more work on? And did the meeting meet your expectations?

Companies need to Follow the Rule of 1s

The secret to engaged and diverse boards is to mix up their membership more than most companies do. Our Board Benchmark study at Bolster indicates that the vast majority of private company boards have no independent directors at all—only founders and investors—and every year, the vast majority of the “open independent seats” specified in those companies’ charters go unfilled. 

It’s hard work hiring a new independent board member, and it rarely rises to the top of the CEO’s priority list. But the more independent the board is, and the more diverse the board is in every way (in terms of demographics as well as experience and background), the more robust the conversations around the table become, and the more valuable the board is to the CEO.

My Rule of 1s for building highly effective boards is simple:

  • Add independent directors to your board on Day 1
  • Try to limit your Board to 1 founder/team member
  • Then, for every 1 investor on your board,
  • Add 1 independent director

A great board is one of a company’s greatest assets. A weak board can kill a company. A mediocre board is just a waste of time. There’s no question that running an effective board, or serving as an effective director, takes serious time and energy and diligence. But that’s not a reason not to try.

(This post first ran on TechCrunch+ and is also running on the Bolster blog)

Sep 22 2022

The Impact of a Good Coach

I’m pretty close to the executive coaching world. My wife Mariquita is an extraordinary CEO coach. I’ve worked for decades with Marc Maltz from Hoola Hoop, who helped me transform everything about how I lead organizations. I’ve been friends with Jerry Colonna of Reboot fame for years (I did a fun podcast with Jerry last year called “Everyone is Scalable). I’m pretty good friends with Chad Dickerson. Bolster’s marketplace helps place CEO coaches and even has a programmatic approach to coaching and mentoring called Bolster Prime. The list goes on.

My friend Mitch, a fellow baseball coach, gave me a fun book a couple years ago that is a page-a-day called Coach: 365 Days of Inspiration for Coaches and Players, by Matthew Kelly. It’s a compilation of quotes. Some are better than others. But I just love this one from a couple weeks ago. While obviously it is in the sports context, the sentiments are the same around executive coaching.

Marc and I had one senior executive who we worked with years ago. They had significant personality and style issues that weren’t working well in our culture. They were abrupt, needlessly angry, and cultivated relationships based on fear, not based on trust. Marc and I were tearing our hair out trying to give this person feedback and coaching. Nothing was working. Then I delivered a 2×4 between his eyes. They argued with me and Marc and said that the problem was us…not them. That we were soft.

Two days went by. Then we met with them again. They came into the meeting visibly upset, shaking their head and a bit choked up. They opened the meeting by saying, “I went home and complained to my spouse about your feedback. And my spouse told me that, actually, you are right, and that I should ask my kids. My whole family feels the same way you do. More than my job is at risk — my marriage and family are at risk, too.”

Months and years later, with a ton of coaching and feedback and support from Marc and me and the rest of our executive team, this person had really turned it around. They were doing better at work. They were doing better at home. The work was long and painful and not without its bumps and backtracks. But the person made changes that were meaningful and permanent to all their relationships, not just something in the moment at work. It’s a clear case of this quote — coaching changed his life.

As I’ve said before, People are People. It doesn’t matter if you’re at home or at work. It doesn’t matter if you’re a B2C person or a B2B person. While there are some prominent examples of individuals throughout history who have very different work and home personae (John D. Rockefeller is one that comes to mind, but I’m sure there are other famous ruthless businesspeople who were empathetic and loving spouses and parents), most of us are simply humans, works in progress. We learn something in Context A, and it’s part of us when we are also in Context B.

The impact of a good coach goes way beyond how you lead your organization.

Sep 15 2022

Best and Worst Practices (Plus FAQs) for Layoffs

Short of declaring failure and shutting down your company, laying off employees is the worst thing you may have to do as a startup CEO. I’ve had to lay people off on three separate occasions. It was difficult and emotional—those days were the worst of my career, and probably rank in the top 10 worst days of my life, period. This isn’t firing for cause—employees aren’t being asked to leave because of their own failings. They’re being asked to leave because the company can no longer afford to keep them. It’s not their fault.

It’s a truly awful process. Some CEOs will fall into the trap of thinking that because it’s invariably messy, it doesn’t matter how you do it. I couldn’t disagree more. Layoffs are bad, but how you handle them makes all the difference in the world. Here are a few best and worst practices for orchestrating layoffs.

Best Practices

1. Cut earlier and deeper than you have to. You really, really don’t want to go through this a second time. Assume you have less runway than you anticipate, and cut early. Cut more employees than you think you need to in order to reduce the risk of a second round of layoffs. Things are always worse than they look, even when the situation is bad enough to consider layoffs. Financing will take longer than expected to come through, receivables will dry up, and so on. 

2. Remove poor performers. You have no choice but to remove people if their positions are being cut altogether, regardless of performance. However, you can also take this as an opportunity for some major house cleaning. Just be sure to work with someone (a lawyer) who can help you navigate the legalities—particularly if you’re dealing with employees outside the US. 

3. Plan your talking points in advance of meetings. When I’m planning all-hands meetings, I tend to write bullet-point notes and talk freely instead of scripting my comments—but not for this. A round of layoffs is likely to be one of the most emotional moments of your career, and when you face your employees to deliver the news, you won’t be in your usual headspace. Don’t wing it. Plan everything you’re going to say—both to the individuals being let go and to your team as a whole—in advance. How you handle these meetings will depend on the size of your company and how many layoffs you’re doing. Regardless, you want to communicate respect for and appreciation of your employees throughout the process. 

4. Follow layoffs with an all-hands meeting. Layoffs are emotional for the entire team. Follow up with an all-hands meeting to explain what happened, why you made the choices you did—preferably with metrics to back up your decisions—what’s next for the company, and whether people who weren’t laid off are at risk in the future. (Be honest!) Ideally, the people you’re laying off should be included, too. You want to honor and thank them in as public a forum as possible. For those who remain, it’s important to cultivate security and trust. However you’re communicating with your employees, you’ll need to increase your efforts, and clarity is always better. Let them in on the state of the business, financials, and expectations. You don’t want to skip over the pain that comes with layoffs, but you do need to be prepared to move forward effectively. 

5. Treat employees who were laid off with dignity and honor the work they did. This will come into play when we talk about what not to do, but it’s important to remember that they’re being laid off for no fault of their own. One meaningful thing you can do is help people find their next step. Promoting the profiles of your former employees on job boards, portfolio lists, etc., offering your own connections if it’s relevant, or giving excellent referrals when you can are all great places to start. Severance is also key. Be sure to consult your board and follow your company policies, if you have them, then be as generous as you can afford to be. If you can offer a safety net or bridge, do so. 

These folks will still be alumni of your company, so the way you handle them personally will impact how they talk about the organization, rate you on Glassdoor, and refer to you as a leader. Every step of the process matters—whether it’s how you broke the news, how public things were, how helpful your team was, how much you paid—and will impact your company’s brand as an employer and your own reputation as a CEO. 

Worst Practices 

1. (Per above) Do not assume, because layoffs are awful and messy no matter what, that it doesn’t matter how you do it. It absolutely matters. 

2. Do not treat the people you fire like criminals. Don’t hire security guards or bring boxes into the office before breaking the news. Think very carefully about what systems you need to restrict access to, when, and whether there are any loopholes. Sure, you don’t want someone to be able to download a whole list of contacts from HubSpot. But do you really want them to be cut off from their email, calendar, and personal contacts? Shouldn’t you work with them to set up an autoresponder or figure out what happens to their email?

3. Do not promise this will never happen again. You can’t predict the future. You can say “we made the best decision possible, so that hopefully we won’t have to do this again.” Offer reassurance through facts and transparency rather than empty promises. 

4. Do not delegate the responsibility for deciding to lay off employees. As the CEO, this decision is yours to own. Also, do not blame someone else or the economy. Circumstances contribute, but at the end of the day, the buck stops with you, and again, you’re the one making the decision. 

5. Do not make mistakes about who is on which meeting invitation list or which employment list. Double check the list yourself, then have someone else check it. 


I held a webinar recently with about 20 CEOs on this topic, and there were a number of questions that came up with interesting crowdsourced answers. Here are some snippets of some of them:

Q: How much severance is the right amount?

A: This is impossible to generalize—if you’re really out of cash, you may have your hands tied. If you can stick to your normal policies, you should. Companies represented on the call tended to give 1-2 weeks per year of service. Other thoughts that came up were: (a) offering a long post-termination exercise period for vested options, (b) accelerating some vesting, (c) creating a Salary Bridge program, which we did once at Return Path. The Salary Bridge program offered people an additional X weeks of continuing severance beyond the standard package if they still hadn’t found a job (but were trying and could show us they were trying) after their severance ran out. Very few people needed this, but the goodwill from offering it was huge.

Q: Have you ever considered salary cuts?

A: Yes. Usually a big layoff will come with some kind of salary cut for those who are staying, even if it’s just executives or just you as the CEO (which is more symbolic than anything else, but symbolism matters). Companies also had experience with doing salary cuts and reinstating the salaries as soon as the economic situation improved. One company talked about doing a 5% salary cut but then offering everyone a 10% bonus based on company financial milestones. In situations like this, it’s also a good idea to share metrics. How many jobs are you preserving by making cuts? 

Q: Do voluntary termination programs work? 

A: They might make you feel better, but be wary of doing them lest you lose key people you don’t want to lose!

Q: Can I expect additional employee attrition after a layoff?

A: Almost certainly. Any time you jolt the system, you’ll produce some unintended consequences. People will feel less stable in their role. Do your best to reassure key employees—even to the point of bringing a couple of them into the know immediately ahead of a layoff—so you don’t lose more people you don’t want to lose. Be wary of offering additional compensation or bonuses for them to stay, unless you are promoting them into expanded responsibilities (which can make sense if you’re consolidating things). Offering some people a raise “for no reason” while you’re letting other people go isn’t a great look.

Q: What about customer communications?

A: Our group was very mixed on whether or not you should do proactive external communications about a layoff. If you run a B2B organization, being a little more transparent with customers shows them you care about them—and gives you an opportunity to talk to them about any changes that might affect them, their service team, or their service levels. In a B2C organization, you’re likely either going to do something public like a short, empathetic blog post, or nothing at all. In all cases, please make sure you have a well developed internal FAQ and clear policies about who can and can’t talk externally as a company representative before doing a layoff so you’re not caught flat-footed.

Layoffs are messy and unfortunate, but you can still handle them artfully as a leader. How you handle layoffs will impact how your company recovers, it’ll impact your reputation as a CEO, and most importantly, it’ll impact the lives of the employees you laid off. I talk a lot about having a people first culture. One of the things I’ve learned about building companies with this in mind is that it’s got to be true all the way through. Even when you resort to layoffs, the people come first. 

(This post also appeared on the Bolster blog.)

Sep 8 2022

When to Hire Your First Chief Revenue Officer

(Post 1 of 4 in the series on Scaling CROs)

In most startups, the founder is the first salesperson and while it may be difficult to let that go you’ll eventually scale, add sales reps, or maybe some form of a Sales Manager once there are more than a couple of reps.  In Startup CXO our Return Path CRO, Anita Absey, wrote about the journey of startup sales, from “selling on whiteboard” to “selling with PowerPoint” to “selling with PDF.” I encourage you to read that section if you’re wondering about hiring a CRO, but all of the hiring of sales reps and (possibly) a sales manager happens during what Anita calls the “White Board” stage as you’re beginning to transition to “Selling with PowerPoint.” 

Selling from a White Board means that you are essentially working with an interested potential customer on a custom and conceptual sale; selling from PowerPoint means that you are selling tailored solutions—you’re no longer at the discovery stage. Selling from either the White Board or Powerpoint stage is fine for an early-stage company, but eventually you’ll want to scale and hire your first CRO. Here are some of the telltale signs that will help you figure out if you should bring in a CRO.

First, you’ll know it’s time to hire a CRO when you’re nervous about HOW you’re going to make this quarter’s number — not just that WHETHER or not you’ll make it (since you should know that as much as anyone). Another sign that it’s time to hire a CRO is when you aren’t clear what the levers are, or what the pipeline/forecast details are, to hit those quarterly numbers. 

If you are spending too much of your own time managing individual deals and pricing, or teaching individual reps how to get jobs done, that’s a clear indicator that a CRO is needed. If your board asks you if you’re ready to step on the gas and scale your revenue engine (e.g., move from Powerpoint to PDF), and you don’t have a great answer and aren’t sure how to get to one then you need to hire a CRO.

A fractional CRO can add a lot of value, especially at a small volume where a full-time CRO would be overkill. Or, if your sale is very complex or to a very senior buyer, and a more junior sales team needs a fair amount of deal support from above, a fractional CRO makes a lot of sense. Sometimes a fractional CRO can help you enter a new adjacent segment (e.g., mid-market going to enterprise), and then you’ll need a seasoned professional to help translate sales processes from one segment to the other while keeping the initial segment running smoothly. 

If you’re not sure what kind of sales leader you’ll need long-term and full time because you’re not at enough scale yet, a fractional CRO can help you “try before you buy.” You can try out a specific type of revenue leader to see if that type works, for example, sales only, sales + customer success, manager of hunters, or builder of a high velocity sales engine, to name a few different options.

Hiring a CRO will definitely free up time for founders and allow them to work on other things that drive the business, without worrying about sales.

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

Aug 25 2022

Double Book Short: Framework of Frameworks

I love me a good framework. And Geoffrey Moore is the kind of good product/marketing frameworks for technology companies. Moore’s Zone to Win: Organizing to Compete in an Age of Disruption is a must-read for anyone managing a larger technology organization (start reading it when you get to 200-250 people – it’s never too early to worry about disruption). More important, it’s really a companion book or coda to Escape Velocity: Free Your Company’s Future from the Pull of the Past, so if you haven’t read that one, start there and read both sequentially. Zone to Win is quite short and punchy, and it doesn’t disappoint.

I can’t believe is that I never blogged about Escape Velocity before since it was a very influential book in how we managed a bunch of things at Return Path in the later years when we got larger and were more in “disrupt or be disrupted” mode. I’ll start with the essence of that book before I move onto Zone to Win. Escape Velocity‘s principal framework is to divide the different product lines/lines of business you have into three planning horizons:

  • Horizon 1 (H1): Current businesses that should be profitable and sustainable
  • Horizon 3 (H3): Nascent R&D efforts with the potential to be disruptors or game changers
  • Horizon 2 (H2): The bridge between H1 and H3 where an R&D effort that is taking off is scaled and hopefully achieves the eponymous Escape Velocity

The essence of the book is to talk about how larger companies become completely slavish to H1 businesses, their cash cows, and struggle to escape from their pull, whether that’s internal resource allocation or customer-driven demands. Failure to innovate properly beyond H1 businesses is why companies die. But the rest of the book is a lot less memorable, and it doesn’t quite prompt you into action.

That’s where Zone to Win comes in, and it helps me understand where we really got a couple things really wrong at Return Path (as an aside, Moore once met my Return Path cofounder George at a conference, and when George described our business to him, he said “Ah, a blue collar business. Those can work, too.” I think I understand what he meant by that, although it doesn’t sound like a compliment!)

In Zone to Win, Moore shows you how to put the three Horizons into action by creating an overlay framework to managing your company to help optimize all three zones simultaneously. The four zones are:

The key takeaways for me from this framework as well as the notes of where we got things wrong at Return Path, even while acknowledging that we had to play across H1, H2, and H3 simultaneously, were:

  • Performance Zone: Managing your main H1 business in a way that drives growth and customer success for the long haul
  • Productivity Zone: Managing your main H1 business for optimal profitability and scalability
  • Incubation Zone: Starting new H3 businesses and hoping they work
  • Transformation Zone: Getting your H3 business through H2 and into H1 to the point where it’s at least 10% of your overall revenue

What we got right at Return Path was first recognizing that we needed to incubate new businesses as the growth in our core business started to slow down, as well as recognizing that we needed to step up our game in managing the core business for performance. So, Moore would say something like “congratulations, you drew up the correct strategy.” But we fell down on implementation for reasons in three of the four zones. Our problem with the Performance Zone is that we discovered the three horizon model too late — there were several years where we were running R&D experiments in the middle of the core business, which created chaos. By the time we got religion around it, we were constantly playing catch up redesigning our management processes — like the teenager still wearing his kid clothes looking awkward and misfit. In the Productivity Zone, we did invest in productivity, but we weren’t aggressive enough about insisting on End of Life for some programs or products, and and we were bogged down by a convoluted legacy implementation of our CRM system that we never wholesale fixed. But the biggest problem we ran into was in the Transformation Zone, where we tried to jam two new businesses through that zone at the same time instead of focusing all our energies on one. I bet we could have pulled off even more of a transformational success with our security business (the one further along) if we hadn’t also been trying to get our consumer insights business through H2 at the same time. At least Moore notes that’s the hardest zone to get right, so I don’t feel quite so dumb.

There were probably other exogenous factors that caused us to fall down on implementation, too, but I think this had a lot to do with it. And don’t get me wrong, Return Path was a success in the end. It just could have been more successful if we had caught this book and adhered rigorously sooner. It was even published in time — somehow we just missed it. We were lured by customer traction and market pull into thinking we could do both. And it’s certainly possible that we were advised against this by one or more of our board members and plowed ahead anyway.

Moore is a masterful writer. If you haven’t read Crossing the Chasm or Inside the Tornado, for example, if you’re a GenZ founder and you think “wow those books came out before I was born, they can’t be relevant,” you should start by reading them. They’re still 100% applicable today, and Moore’s subsequent editions have updated some of the case studies, even if not totally contemporary — and these are worth reading even as a raw startup (in fact, especially as a raw startup). But once you finish those and your business gets larger, go straight into Escape Velocity and be sure to add on Zone to Win.

Aug 18 2022

The Evolution of Feedback in Our Organizations

Across 22 years and two companies now, our system of giving performance feedback has evolved significantly. I thought I’d take a pass at chronicling it here and seeing if I had any learnings from looking at the evolution. Here’s how things evolved over the years:

  • Written performance reviews. The first year of Return Path, we had a pretty standard process for reviews. They were more or less “one-way” (meaning managers wrote reviews for their direct reports), and they only happened annually.
  • Written 360 reviews. We pretty quickly moved from one-way reviews to 360s. I wrote about this here, but we always felt that being able to give/receive feedback in all directions was critical to getting a full picture of your strengths and weaknesses.
  • Live 360 reviews. In addition to the above post/link, I wrote about this a bit further here and here. The short of it is that we evolved written 360s for senior leaders into facilitated live conversations among all the reviewers in order to resolve conflicting feedback and prioritize action items.
  • Live 360 reviews with the subject in the room. I wrote about this here…the addition of the subject of the review into an observer/clarifying role present for the facilitated live conversation.
  • Peer feedback. At some point, we started doing team-based reviews on a regular cadence (usually quarterly) where everyone on a team reviews everyone on a team round-robin style in a live meeting.

The evolution follows an interesting pattern of increasing utility combined with increasing transparency. The more data that is available to more people, the more actionable the feedback has gotten.

The pluses of this model are clear. A steady diet of feedback is much better than getting something once a year. Having the opportunity to prioritize and clarify conflicts in feedback is key. Hearing it firsthand is better than having it filtered.

The biggest minuses of this model are less clear. One could be that in round robin feedback, unless you spend several hours at it, it’s possible that some detail and nuance get lost in the name of prioritization. Another could be that so much transparency means that important feedback is hidden because the people giving the feedback are nervous to give it. One thing to note as a mitigating factor on this last point is that the feedback we’re talking about coming in a peer feedback session is all what I’d call “in bounds” feedback. When there is very serious feedback (e.g., performance or behavioral issues that could lead to a PIP or termination), it doesn’t always surface in peer feedback sessions – it takes a direct back channel line to the person’s manager or to HR.

The main conclusion I draw from studying this evolution is that feedback processes by design vary with culture. The more our culture at Return Path got deeper and deeper into transparency and into training people on giving/receiving feedback and training on the Difficult Conversations and Action/Design methodologies, the more we were able to make it safe to give tough feedback directly to someone’s face, even in a group setting. That does not mean that all companies could handle that kind of radical transparency, especially without a journey that includes increasing the level of transparency of feedback one step at a time. At Bolster, where the culture is rooted in transparency from the get go, we have been able to start the feedback journey at the Peer Feedback level, although now that I lay it out, I’m worried we may not be doing enough to make sure that the peer feedback format is meaningful enough especially around depth of feedback!

Aug 11 2022

What Men’s Rooms Can Teach Us About Leadership and Management

I hope this post doesn’t gross anyone out or offend anyone. I admit it’s a little weird, and that it’s more accessible to men. Hopefully everyone can get my point, even if men get it a bit more. I’m channeling Brad as I write this. So bear with me.

Here is a picture of a men’s room with floor mats under the urinals.

The difference between using a men’s room that has floor mats and using a men’s room that does not have floor mats is profound in multiple ways. I’ll leave out the specifics, but you can imagine the comparative experiences if you haven’t had one or both.

A really good floor mat, from a quick scan of Amazon and Uline just now, costs $11 if you buy in bulk and is built to last 4-6 weeks. That gives us an annual per urinal expense of about $100 – trivial in the scheme of maintaining an office, restaurant, or place of business.

But here’s the thing. These floor mats are few and far between. I don’t have scientific research on the matter, but I’d guess that between 1 in 5 and 1 in 10 places of business have them. Maybe even fewer.

So, urinal floor mats are (a) cheap, (b) easy to acquire, and (c) make a profound difference in the environment. And yet, they are only have 10-20% market penetration at most.

That market penetration is not far off from the prevalence of very good leadership and management in business. I hear stories all the time from executives about absolutely terrible leadership practices. I also hear plenty of stories that aren’t awful, but are evidence of non-leadership or non-management. The experience of working for a good manager, or in an organization with strong leadership, is profoundly different than working with the absence of those things.

To complete the analogy, good management and leadership are also (a) cheap, (b) easy to acquire, and (c) make a profound difference in the work environment. Sure, you can’t buy good leadership online, but it’s not all that difficult to be a caring, supportive, transparent manager. Heck, there’s even a book called The One Minute Manager.

So why the low market penetration of both? It makes no logical sense. It’s not as if most people haven’t had the experience of using a urinal with a floor mat…or of having a really good leader or manager. It’s not as if leaders and decision makers don’t appreciate those things themselves.

The answer boils down to three simple points that anyone who is a manager or leader can do, any day:

  • You have to pay attention
  • You have to care
  • You have to act

Great leaders and managers exhibit all three of these traits. They pay attention to things around them, noting that Everything is Data. They care about people, about experiences, about impressions, about reputations. And when they notice that something is off – however small it is – they care enough to remember and then take the time to act. To make a small change. Send an email. Have a quick conversation. Make a suggestion. Give someone quick praise or constructive feedback.

And to come back to where this post started – it’s also not that hard to have a nice men’s room at your office or business or restaurant. You just have to pay attention to the fact that it’s a much better experience to buy floor mats. You have to care about the experience in the men’s room (for yourself, for employees, for customers, for vendors, for visitors). And then you have to act and either buy the stupid mats or ask an office manager to do the same!

Aug 4 2022

Our Operating Philosophy – the Mostly Self Managed Organization (MSMO)

Last week, I wrote about the concept of the Operating Philosophy, and how it fits with a company’s Operating Framework and Operating System and defines the essence of who you are as a company…what form of company you are.

While we had a loose Operating Philosophy at Return Path, we never really crisply articulated it, and that caused some hand-wringing at various points over the years, as different people interpreted our “People First” mantra in different ways. So this time around at Bolster, we’re trying to be more intentional about this up front. We have labeled our company a “Mostly Self Managed Organization” or MSMO (pronounced Miz-Moh). We made those up.

Our Operating Philosophy – we are a Mostly Self-Managed Organization, or MSMO (pronounced Miz-Mo, a term we just made up). The MSMO is the product of years of work, research, practical learning, and thinking on our part.  Self-Management has been important to me my whole career as a manager and leader.  Over the last 15 years, the team and I have studied various forms of self-management with interviews and onsite meetings at Netflix, Gore, Nucor, Morningstar, and Zappos.  While we implemented some aspects of it at Return Path, we are trying to take the implementation a step further here at Bolster from the beginning.

Of all those companies, what we’re doing is probably closest to the Operating Philosophy of W.L. Gore & Associates, which you can find written out online without a name but with the description that “individuals don’t need close supervision; what they need is mentoring and support.” The embodiments of the Operating Philosophy at Gore may be different from those we create at Bolster, but the essence of the philosophies is pretty similar.

Why a MSMO?  We employ smart people, and smart people crave autonomy, purpose, and mastery (according to Daniel Pink) and do their best work when they have those things in alignment.  

So, how do we define self-management at Bolster?  We aren’t going to be a DAO.  I don’t think that model works for a for-profit multifaceted corporation – complete Self-Management is too chaotic.  Leadership and mentorship matter and make a difference in guiding strategy, critical decisions, and careers. Holocracies or other unnamed structures like that of Morningstar are ok, but they are so rigidly ideological that they require an immense amount of work-around, or scaffolding, to be practical.

But we aren’t a traditional fixed top-down hierarchy, either.  We are going to run the business in a way that lets people co-create their work and be responsible for driving their own feedback and development with a support structure.  That’s the ideology we have. Letting talented people loose to do their best work is critical; but leadership, judgment, and experience matter, too. If not, why bother having a CEO, or a VP of anything? Why not just pay everyone the same thing and hope they can all figure out the complexities of the business together?

We believe the MSMO is the best operating philosophy to allow high performers to do their best work. 

At Bolster, we are leaning into things like social contracts, peer feedback, career mentorship, individuals translating our Operating Framework into priorities and work, flexible work streams and team leadership, instead of fixed permanent hierarchies, rotating chairs of key company meetings, and market-level-based compensation.  

What we are steering away from are things like traditional titles, micromanaging or overmanaging, traditional performance reviews linked to compensation and complex incentive compensation structures, and fixed organization boundaries and structure.

We’ll see if our MSMO Operating Philosophy works. If not, we’ll iterate on it. That’s the good thing about adherence to an ideology of philosophy as opposed to an ideology of practices. Who knows – maybe the MSMO concept and even its quirky name will catch on!

Jul 28 2022

The Concept of the Operating Philosophy

I’ve always been a big believer in the Operating Framework and the Operating System as two of the management underpinnings behind every well run company.

The Operating Framework is the company’s Mission, Vision, Values, Strategic Objectives, and Key Metrics. Companies have all sorts of different labels for this, from Balanced Scorecard to Salesforce’s V2MOM to Patrick Lencioni’s 6 Questions. It’s what you have to define up front, refresh annually, and tweak quarterly so that people in the company are aligned and know where you’re going.

The Operating System, as I wrote extensively about in Startup CEO, is the collection of practices, meetings, mailing lists, routines/rhythms, and behaviors that your company and team use and depend on to run the business on a day to day basis. It’s what you have to put in place and tweak as needed so work gets done efficiently – the thing that turns the sprint of a raw startup into the marathon of a scaling business.

But there’s a third leg to the stool of company management underpinnings that’s often overlooked and underappreciated – the company’s Operating Philosophy. The Operating Philosophy is the intellectual underpinning of how you want to run and lead the business. It’s related to, but different from, your company’s values. Think of it as the essence of how you want to work and shape the work of others…what defines your form of company.

You can run a company perfectly well without a clear Operating Philosophy, especially with a tight Operating Framework and Operating System in place. But my guess is that you have one, you just haven’t articulated it yet, and you might benefit from doing so. At least that was our experience where we had an undefined but real one at Return Path and have now tried to define one front and center at Bolster.

A useful way to think about these three legs of the stool is the analogy of government (bear with me on this and pretend like our government in the US isn’t quite as dysfunctional as it is at the moment). Our Operating Framework is the Constitution – it lays out the broad contours of what our government does. Our mission, vision, and values. Our Operating System is the collection of policies, practices, and programs that run the country, from the timing and cadence of elections, to the ways the three branches of government enact and execute policy, to the ways state and local governments fit in. Our Operating Philosophy is the Declaration of Independence. It’s our essence. It is what separates our form of government from other forms of government. We are a Representative Democracy, a Constitutional Federal Republic. We hold these truths to be self-evident, that all men are created equal, that they are endowed by their Creator with certain unalienable Rights, that among these are Life, Liberty and the pursuit of Happiness. That to secure these rights, Governments are instituted among Men, deriving their just powers from the consent of the governed.

Some examples? Zappos is a Holocracy – defined as a system of corporate governance whereby members of a team or business form distinct, autonomous, yet symbiotic, teams to accomplish tasks and company goals. The concept of a corporate hierarchy is discarded in favor of a flat organizational structure where all workers have an equal voice while simultaneously answering to the direction of shared authority. Patagonia (and lots of other companies) is a Delaware Public Benefit Corporation (PBC or often called a B Corporation), which must by law follow Stakeholder Capitalism and not Shareholder Capitalism. Plenty of crypto organizations are set up as DAOs (Decentralized Autonomous Organizations), which is a group of people who come together without a central leader or company dictating any of the decisions, built on a blockchain using smart contracts and a currency of tokens that give them the ability to vote on decisions that are made around how the pool of money is spent and managed.

Hopefully that makes sense. Next week, I’ll talk about our Operating Philosophy at Bolster.

Jul 21 2022

Giving Away Credit – Added Rationale

I just finished up a coaching call with a late-stage CEO client, and we were talking about a situation where he helped tee up a couple successes for a new senior executive on his team and then promptly gave the exec credit for the successes. That’s good form as a leader – you take the blame when things go wrong but give away credit when things go well.

But my client articulated a selfish reason to this that goes beyond the “good leadership form” argument that I’d never thought of before:

“When you give them the credit, you win twice.”

What he meant by that is that you get your first win when you bolster the person on your team by giving them the win. And you get your second win when others (the rest of the team, your board, etc.) see the goodness that happened and realize that it happened on your watch as the CEO — either by hiring the person who got the credit, or by orchestrating the broader scenario.

After all, who doesn’t want to win twice?

Jul 14 2022

Second Lap Around the Track

I wrote a little bit about the experience of being a multi-time founder in this post where I talked about the value of things like a hand-picked team, hand-picked cap table, experience that drives efficient execution, and starting with a clean slate. The second lap around the track (and third, and fourth) is really different from the first lap.

Based on what we do at Bolster, and my role currently, I spend a lot of time meeting with CEOs of all sizes and stages and sectors of company, as they’re all clients or prospects or people I’m coaching. Lately, I’ve noticed a distinct set of work and behaviors and desires among CEOs who are multi-time founders and operators that is different from those same things in first-time founders. Not every single multi-time founder has every single one of these traits, but they all have a majority of them and form a pretty common pattern. I’ve noticed this with non-profit founders as well as for-profit ones.

  • They have an Easier Time Recruiting team members and investors. That may sound obvious, but there are significant benefits to it. They also tend to have Much Cleaner Cap Tables, because they lived the horrors of a messy cap table when they exited their last company without thinking about that topic ahead of time!
  • They have a Big Vision. Once you’ve had an exit, whether successful or not or somewhere in between, you don’t want to focus on something niche. You want to go all-in on a big problem.
  • They are interested in creating Portfolio Effect. A number of repeat founders want to start multiple business at the same time, are actually doing it, or are creating some kind of studio model that creates multiple businesses. Once you have a big team, a track record with investors, and a field of deep expertise, it’s interesting to think about creating multiple related paths (and hedges) to success.
  • They are driving to be Efficient in Execution and Find Leverage wherever they can. One multi-time founder I talked to a few weeks ago was bragging to me about how few people he has in his finance team. At Bolster, our objective is to build a big business on a small team, looking for opportunities to use our own network of fractional and project-based team members wherever possible.
  • They are Impatient for Progress. While being mindful that good software takes time to build no matter how many engineers you hire, repeat founders tend to have fleshed out their vision a couple layers deep and are always eager to be 6 months ahead of where they are in terms of execution, which leads me to the next point, that…
  • They are equally Impatient for Success (or Failure). More than just wanting to be 6 months ahead of where they are in seeing their vision come to life, they want to get to “an answer” as soon as possible. No one likes wasting time, but when you’re on your second or third company, you value your time differently. As a friend of mine says in a sales context, “The best answer you can get from a prospect is ‘yes’ – the second best answer you can get is a fast ‘no’.” The same logic applies to success in your nth startup. Succeed or Fail – you want to find out fast.
  • They are Calm and Comfortable in Their Own Skin. At this stage in the game, repeat founders are more relaxed. They know their strengths and weaknesses and have no problem bringing in people to shore those things up. They know that if things don’t work out with this one, there’s more to life.
  • They are stronger at Self Management. They are more efficient. They exercise more. They sleep more. They spend more time with family and friends. They work fewer hours.

Anyone else ever notice these traits, or others, in repeat founders?