When the CEO Becomes a Soldier

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We think of the CEO as the corporate equivalent of a general – planning out the strategy, deciding which battles to fight, determining what resources to apply in the pursuit of which efforts, leading teams into battle and motivating the organization. The parallel between general and CEO is at best an incomplete one. In a startup, the CEO is as much soldier as general.

Superior execution is too important in a startup for the CEO to be only a leader. In its earliest stages, startups require everyone to contribute 200% and the CEO is no different.  Yet as the company grows in people, products, revenues and complexity – there is a tendency to assume that the CEO morphs into the order-barking general.  Nothing could be further from the truth.  Sure, as a company scales, the leadership traits of the CEO become increasingly important, but just as important is the CEO’s ability to step back into the role of individual contributor, and at times, just follow orders. I’ve learned that the assumption of most of the organization will be to always assume that the CEO is acting in a leadership capacity, so communicating that I’m playing one of the other roles proactively becomes extremely critical so that others can step up to the other roles. Here are some scenarios where I think about being an individual contributor even as BloomReach becomes a Company of 250 people:

  •  Selling a big deal: The customer always wants to talk to the CEO and well-placed involvement in driving a big deal could shorten a sales cycle by months or even create a deal where none existed. At the scale we’ve achieved, I’m not likely to be close enough to the details to drive the strategy around closing the deal. I’m more focused on taking orders from the sales rep or the broader account team.
  •  Closing a key employee: The recruiting team has likely laid a lot of the foundation for the discussions and the interview process is probably nearly complete. My job now is to help close the deal. There are certain questions from a candidate (value of the equity, vision of the company) that a CEO is best placed to answer. Being involved in closing a hire can make a big difference.
  •  Tackling a difficult conversation with a customer or an employee: Maybe our system has failed a customer. Maybe we have not delivered on an employee’s expectations.  By the time the CEO has been one of these situations,he or she is playing the role of firefighter. In situations of this kind, while I may not have been directly involved in the problem build-up, it becomes my job to calm the situation and identify a fruitful next step (which at times can be to part ways).
  • Building consensus around a key product decision: In this role, the CEO has become product manager. Often, in the murky world of product strategy, key stakeholders can have different perspectives on direction.  Ideally, the product managers and product marketers drive the decision.  But sometimes, that just doesn’t happen.   It then becomes the CEO’s role to gather the data, drive to a decision and then enroll those stakeholders in the decision.
  • Being a thought-partner to key executives and leaders: There are plenty of cases where the CEO is advisor, not decision-maker. Maybe a team is thinking about restructuring and considering alternatives. Maybe an investment decision is being made. There are plenty of decisions that shouldn’t be made by the CEO, but the CEO can serve as a counselor – provided he or she is comfortable knowing that the counsel may or may not be taken.  The culture of the organization needs to permit dissent – otherwise advice can easily be misinterpreted as orders.

The cases of CEO as soldier are often ones where the leverage gained from being an individual contributor can create outsized outcomes for the company and where the CEO is uniquely placed to deliver those outsized outcomes (i.e. it’s unlikely someone else can be found to play that role as effectively).  I’ve tried to be extremely deliberate about when I’m playing the role of leader, when I’m playing the role of advisor, and when I’m playing the role of soldier.   It’s important that the soldier role not be the dominant one, otherwise the CEO will crowd out others and ignore critical leadership duties.

Nonetheless, getting back to being a situational soldier can be extremely empowering for leaders as the team grows. While management can be fun, it can also be wearisome and the subset of days when one gets to own a product decision, own a sale or own a hire, can very much feel like a return to one’s roots, in the trenches.

Image from Army Ten-Miler Salute by The U.S. Army licensed under CC by 2.0

The Evolution of One Entrepreneur’s Vacations


I know your first question.  Do entrepreneurs take vacations?  Absolutely.  I just got a chance to spend four days in a beautiful Hawaiian beach town and it made me reflect on the evolution of my vacations as a founder/ceo.  The vacation-eschewing, Jolt-cola-drinking, 24-hour-hacking founder culture is primarily the stuff of urban legend.  Entrepreneurs are like everyone else.  They burn out.  And without vacations, they burn out faster.  Any entrepreneur that believes in never taking vacations is either lying or the leader of a company that simply won’t be around very long.  Vacations are as important to the success of an entrepreneurial venture as work ethic.  In fact, if you can’t check out, you can’t be productive when you’re checked in – and that ultimately impacts your start-up’s success massively.  You certainly can’t connect with family the way you need to – and that impacts your start-up’s success massively too.

But taking a vacation as a founder is REALLY difficult.  You have an emotional connection to the company you started and can’t imagine it surviving even a day without you there.  If you’re like me, you’re typically a workaholic – and get a rush out of working a little harder.  And you live in an ultra-connected world, which means vacationing isn’t as simple as going someplace else.

I took my first vacation as a founder at least about a year and half after we started BloomReach.  We were really small then (fewer than 6 people) and the idea of one of us not being around for a week was impossible to imagine. The likely loss in velocity was just too disconcerting to contemplate.  Things got interesting when I took my first vacation.  I ended up heading to the beach, where I pretty much worked like I was at home.  The early-stage start-up vacation is simply an exercise in transplanting and pretend-vacationing.  The root problem with my early vacation was that I was too much in the flow of critical path items.  Customers needed to be signed. People needed to be recruited.  Products needed to be released. I was a bottleneck to progress in all of them. Whenever I opened my inbox, it had more emails to respond to than I had minutes to type.

As we cross the 225-person threshold at BloomReach, my vacations feel pretty different.  Sure, in Hawaii there were the one or two phone calls I absolutely had to take and re-orient my day around.  There was the occasional mind-wandering from the family back to work.  But for the most part, I checked email about twice a day and didn’t do a whole lot beyond that.  As I was on the plane ride back home – I opened my email and found that I could get through it pretty quickly. It wasn’t that there weren’t critical items for me to tackle – it’s just that none of them could be tackled via an email task list. I had about 5 big problems to think about – like an under-performing team or the long term strategy for one of our product lines or ways to continue to drive incremental growth.  All of them required a lot of thinking, significant in-person communication with key folks, some data gathering and multi-dimensional action.  Most were urgent topics, just not ones that could be tackled at a vacation in Hawaii.  The vacations changed because the role has changed.  We now have a terrific team to tackle the extremely important day-to-day challenges of the Company.  But as the team has grown, structural challenges like the topics mentioned above become more thorny and less easy to address.  Given the nature of how vacations evolve as one’s role evolves, I think an Entrepreneur should also change the way he or she takes them.  In the earlier days – take them a bit more frequently but for short bursts (a long weekend here or there).  The days are long so you need to constantly re-charge but you can’t be away very long.  As the Company grows, take them less frequently but for longer periods of time (perhaps a week or 10 days).  That might enable more of an ability to “disconnect” and greater clarity of thinking to tackle the thorny challenges.

One of my investors, Scott Sandell from NEA, advocated to me that I take a three-week complete check-out vacation every year.  I’m not enlightened enough to be there.  After four or five days, I’m pretty excited to come back to work.  But I do see his point.  As you grow in role and responsibility, the quality of your decisions become a lot more important than the quantity of actions you take.  And that quality requires a clear mind – one that comes from genuine vacations.

Scaling a No-Titles Organization

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Three of the core values of BloomReach are “We”, “Own” and “No Drama.” “We” is about being on shared journey – no individual stars at the expense of the team. “Own” is about acting and behaving like an owner of the company. “No Drama” is about being a team of problem solvers – non-political and collaborative. These cultural values are tightly coupled with the core objective of many early-stage start-ups: creating an environment of little to no hierarchy and maximum creativity. Given that titles are typically a source of hierarchy, the question of how to handle the scaling of the organization while minimally introducing titles is the subject of this post.

Stage 1 – the early days

One of the earliest decisions my co-founder and I made was to establish a principle of “no titles” (full disclosure Ashutosh was always CTO and I was always CEO). The idea was born out of a desire to create an environment where those three values could really take root. In a world of large numbers of VPs, directors, senior directors and managers, the incentive system seems out of whack with the priorities of an early stage start-up. We wanted everybody to be part of “We” – not just the leaders of the company. If titles were eliminated as an issue, everyone could feel like an equal part of the journey. Everyone could feel like they were an owner. And if no one could gun for a new title, the drama quotient would be significantly reduced. Everyone in engineering was “member of technical staff.” People could be paid differently and given different levels of responsibilities – but the lack of hierarchical titles would drive a culture of equanimity. We even went so far as to word every offer letter by function rather than title. People were simply “in sales” or “in marketing.” The standard question we would get is, “How do you recruit great people to a no-titles culture?” By sticking to our guns. If we could come out and say “we have no titles at BloomReach” – it’s pretty hard for a candidate to make an argument that they deserve an exception. And those that walked away on that basis, we were happy to lose.

Stage 2 – “Head of”

As time went by, we got into the “head of” stage of the company-title evolution. We hired a “head of sales” and a “head of product”. The “head of” title was meant to signify leadership, not one’s superior position on the organizational chart. A “head of east coast sales” could report to a “head of sales”. By keeping both titles “head of,” we were continuing to send the message that we were still very much a “We” culture. We could recruit leaders if we needed to, and ensure that the efforts those people were leading could be reflected in the way they described themselves externally. The objective of adding a “head of” title was twofold – provide clarity to the external world on the role of our people and provide clarity internally on who owned a given function. We complimented the “head of” with leads. We had tech leads, marketing leads and product/account management leads. Leads were not titles – they were roles. Someone could be a tech lead for project A and a team member for project B. Stage 2 enabled us to grow up a little bit, just really slowly. And it allowed us to preserve a no-hierarchy culture in day-to-day operational life.

Stage 3 – Directors and Principal Engineers

As BloomReach’s engineering team grew we started to need real people-managers outside of the executive team. We also needed individual role models for the rest of the organization. Directors and principal engineers were born. We have always been very conservative about the criteria for these titles. The people who took them on were already clear leaders – managing complex projects and large teams or providing technical leadership across the company. The addition of directors and principal engineers provided aspirational role models, but still preserved the ethos of a “no titles” world. Since less than 5% of the team had these titles and the bar was so impossibly high – the same behavior of the early days was maintained, albeit with individuals now clearly responsible for the success of others.

Stage 4 – Peer-based promotions

Just recently we took our conservative approach to titling to a new level. As a result of clear feedback from our team that they were hungry for more readily accessible career paths, we introduced the “staff engineer” and “manager” titles in engineering. Though they may make us look a lot more traditional, it was our promotion process that preserved the essence of BloomReach values. The recently rolled out promotion process enabled a team of senior engineers and engineering directors to evaluate the contributions, cultural fit and impact of candidates. They reviewed everything – code, projects, leadership and interaction style. They set the criteria for being promoted to “manager” and “staff engineer.” They debated the merits of each individual and ultimately reached consensus. Importantly, neither my co-founder (our CTO) nor our head of development was present in those meetings. It sent a clear signal: promotions at BloomReach would not be achieved by currying favor with leadership. You succeed by earning the respect of your esteemed colleagues.

Why bother with all of this innovation around titles and promotions? If we were going to end up in the same place as many other companies, why not take the shortcut there? Culture is set in the early days and reinforced over time. Setting a no-titles culture created the collaborative nature of the BloomReacher. Even as titling is introduced, the value system has become so ingrained that it cannot be broken. The conservative approach to titles also ensures that we had the minimum amount of hierarchy needed for a given stage.

The spirit of the “no-titles” organization remains intact today and it is at the heart of everything we do that makes BloomReach healthy– debate, contribution, impact and limited politics. People said it would break over time as the company scaled. We are at 210 people and counting — and I’m still waiting.

Image from Ceramic Hierarchy by Travis licensed under CC by 2.0

The Perfect Board Meeting

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The board meeting needs re-imagination. At most companies, board meetings are either a source of angst for entrepreneurs and investors alike or a source of boredom for those who sit through hours of administrative minutiae. They are either too eventful or not eventful enough. Board meetings are an important communication vehicle and an important force in galvanizing the founders and the management team to step back and evaluate the business from the outside-in.

The perfect board meeting is a problem-solving session. It is a place where smart people with the “inside view” (the management & founders) and people with the “outside view” (investors and independent board members) can come together to solve the thorniest problems in a positive manner.

But lets start with the worst kinds of board meetings:

  • “Peacock” board meetings: The peacock board meetings are spent with each individual around the table showing off. Investors may show-off how much pattern matching capability they have. They may be positioning against each other. Management shows off what an amazing job they’ve done. Neither party has a conversation, and the parties leave keeping a mental score of who won. Peacock board meetings are not only counter-productive, they set up the kind of adversarial relationships that are ultimately destructive.
  • “Show your work” board meetings: In the “show your work” board meetings, every member of the management team comes through and fires up their powerpoint presentation. By the end of the session, everyone is bored and it feels like Physics 101 in a lecture hall of 500 people. No one gets anything out of the exercise and reading the textbook would have been just fine. In these meetings, everyone leaves with a lot of data, but very few people leave with any wisdom.
  • “Administrative” board meetings: Many public boards have become largely administrative – focused on stock compensation plans and auditing guidelines. The boards no longer focus on the key strategic issues of the time. Instead they are focused on liability-protection and ensuring that the company doesn’t screw up, not concentrating on what it takes to enable the company to succeed.
  • “Beat-down” board meetings: In the beat-down board meetings, members spend their time beating on the team. It becomes a venting exercise for the investors and an exercise in spin for the management. Beat-down board meetings destroy trust and ultimately cause decisions to be made for political reasons rather than value-creation reasons.
  • “Tangent” board meetings: Tangent board meetings involve one or more board members hijacking the agenda to discuss a tangent. Often that tangent involves discussing something largely peripheral to the prospects of the business for really long periods of time. Tangent board meetings cause others in the room to check out and represent a terrible waste of time.

So lets get to the perfect board meeting – a meeting between equals, engaged in helping solve the most important issues of the day. The meeting may start with minutes and resolution approvals, but it moves on quickly from there. Next up is a reminder of what was discussed previously, how that ties into today’s agenda and what key decisions have been made by the company. Remember, board members are busy and on a lot of boards. It’s your job to remind them what was discussed and agreed upon. The key performance indicators and operating highlights are discussed – but not in a lot of detail, because they can be sent out in advance. It is important, however, that you not assume that every board member has read all of your material in advance. They likely haven’t; and a common baseline is needed to have a valuable strategic conversation. If you’re spending more than half your Board Meeting baselining, however, that’s too much.

Board members will typically care a lot about sales metrics, revenues, the executive team and financing. You’ll feel like you’re spending a disproportionate amount of time on those topics versus other things that you may care equally about (like product, engineering, culture or marketing programs). Get used to it. Your board meetings are not intended to be balanced portrayals of your mental space. The core of the board meeting should be centered on key strategic questions that you are struggling with: Which market to go after? When to raise money? What are the critical hires to make? How to deal with a macro threat? These are tough questions to discuss with a team of people who are not thinking about them every day the way you are. You will feel like you’re doing a lot of education. That’s OK. If you tee up the discussion well, you’ll get a forest-from-the-trees perspective from a number of the people in your boardroom. They will ask you questions that make you re-evaluate your priorities and your intuition. The best board members will not tell you what to do. But they will offer strong opinions. It’s your job to consolidate those points of view, arrive at a decision and ultimately communicate it back to them (except for the small number of things that actually require a board vote).

The best board meetings are passionate, respectful and inclusive. They are open to the key leaders in the company. They allow for disagreement without personal attacks. The best board meetings are also stage specific. I remember our first board meeting 6 years ago with Ajay Agarwal from Bain Capital Ventures. It was entirely focused on hiring engineers. We’ve since had board meetings focused on people and culture, or financing strategy or go-to-market productivity metrics or strategic priorities or vertical expansion. The topics have to reflect where you are as a business. The best board meetings are continuations of conversations – ideally, you’re speaking to your board members with enough regularity (typically more in the early life of a company than later) that they are not re-learning the business every time.

The best board meetings are brutally honest about the challenges the company faces – typically surfaced by the founders/management and not the investors. The best board meetings keep to the agenda and avoid the many rat-holes. The best board meetings have some amount of cheerleading built into them. Company-building is a marathon and every good marathoner needs cheering along the race. The cheerleading helps the investors stay positive through difficult times and more importantly, it will help you and your team feel like you are all on a special journey. The best board meetings are forcing functions for internal communication and re-evaluation.The process of identifying important topics and preparing materials should cause you to keep perspective on the company’s priorities in the middle of the inevitable operational fires. And they provide an opportunity to reflect those priorities back to your larger team during all-hands meetings or through other company communication vehicles.

By no means has every board meeting we’ve conducted at BloomReach been perfect. I can remember plenty where we were guilty of the “show your work” Board meetings. But we’ve gotten a lot better.

And it goes without saying that the prerequisite to the perfect board meeting is perfect board members. Pick wisely and the rest is learnable.

Image from Board Meeting- Franklin Canyon by tiarescott licensed under CC by 2.0