Part II of this guide laid out strategies to contend with anxiety. Here in Part III, we get into reducing anxiety at the source. Founders anxiety generally results from being overwhelmed, having too much to do, and being adrift in a sea of bad news. Thus in order to improve mental health, founders must learn to be superb leaders and find out how to drive the company forward through the team’s performance rather than their own performance. 

But we’ll begin by considering first how they can better organize their own work. 

Working Deliberately: Project Managing Yourself

There’s so much to do in startups that the decision on what to work on next seems perpetually self-evident. There’s the major goals that we’re way behind on achieving. There are the latest fires that need to be put out. And then of course there’s the fundraising required just to keep us alive. So much of it is staring right at you, so don’t waste any time, just go do it! Given these circumstances, many founders do not waste any time on the “overhead” of organizing their time and instead just have at it, relying on a subconscious set of priorities and tasks that guides their activity blended with reactionary response to the latest emergencies.

This approach, however, is just what founders should not do. First, not providing conscious attention to determining what priorities are results in the founder focusing upon priorities that are not the most important. While “time working” might be maximized, “critical progress,” which is more important, is not optimized.

In addition to working on lesser priority issues, this approach generates significant anxiety-feeding subconscious chatter. Is what you are currently working on the most important thing? Or is it something else? What needs to be done today? Tomorrow? Next week? What are the consequences if you come up short? What items are you forgetting or not aware of? All of these questions are rattling around your mind, generating fear and confusion.

Instead the founder and the company should adhere to a planning cadence: planning goals at the annual level, the quarterly level, and the sprint (~2 week interval) level. Time should be devoted to this planning, and the resulting plans, goals, and then actual performance should be documented. This process enables the founder to let go of the subconscious chatter about all the things that might need to be done, and instead focus completely on what they are doing now, resulting in much higher productivity and output. It also avoids the anxiety generation that comes from this chatter.

Founders can become dopamine junkies. As founders are bombarded with stress and thus cortisol, they can tend to counter-medicate through dopamine, specifically through the little biochemical moments of satisfaction that come when you get stuff done. And being a hyper-achiever, the founder furiously mows down tasks as they arise, feeling that “I don’t know how I’ll ever make this company successful, but if I just get lots of stuff done, that feels better.”

But the founder must resist this chaotic approach. Again it allocates your time suboptimally and it puts you on a never-ending hamster wheel of anxiety. Of course you should revel in the gratification of accomplishment and strive to be super productive. But do it in an organized, conscious way. Have a set of written goals and tasks that steer your work. And maybe, even if just for moments, permit yourself the sensation of crossing off everything on your list and having a sense of being done (of course, you’re not done and there’s more to do, but just bask in it briefly).

Your Job is Leading: Shrinking the Scope of Your Concerns

Founders tend to be overachievers, and so when they take on the mega-challenge of a startup, they go into hyper-achiever mode, and look to crank out accomplishments at a super productive rate. And yes, while being a force of nature can propel the startup forward, it can also become unsustainable as the company grows and the scope of work continues to expand. It also becomes dis-empowering to the team if they see the founder regularly jumping into what should be their areas of responsibility.

Most importantly, as the team grows from a handful of folks to a dozen and beyond, the founder must realize that they, the rest of the team, will always be capable of getting much more done than you, the founder. Thus if the objective is the success of the company, then the most important job of the leader is to lead and to enable the maximum output of the team.

Such focus on leadership is thus what is best for the company. But it is also what is best for the founder. Through forming and leading a team who take ownership for various key outcomes of the business, the founder shrinks the scope of their concerns. Rather than always straining to figure out all of the problems and challenges around the business, the founder can trust that others are doing so and can monitor that the needed progress is being achieved. Thus the worries and fears rattling around the subconscious shrink, and the founder gains the mental health and sharpness required for optimal performance.

The day that a founder starts a new company should be the high water mark of the scope of their responsibilities; thereafter begins a continuous process of shrinking those responsibilities. With every hire those responsibilities should contract and the performance of the company should grow, but that only happens to the extent that the founder is an effective leader.

To be a good leader, we’ll review how the founder must understand what ownership really is, how to hire the right folks who will take ownership, how to delegate ownership across the team, and how to hold these owners accountable and celebrate their wins. Threaded across these founder capabilities is emotional intelligence: the ability to consider the perspective of colleagues and what they need to be successful, the ability to evaluate them on a personal level, and the understanding of what it takes to motivate them and enable them to excel. Many founders are not accustomed to being in such a leadership position and thus need to really focus on developing these skills.

Ownership

In the most fundamental exchange in a startup, the founder (particularly the founding CEO) takes money from investors in exchange for a commitment to achieve the business plan and vision that the founder has laid out. In this exchange the founder takes on a heavy burden. The founder is showing a plan that will provide 10X returns to investors, but the reality is that only a small sliver of startups achieve such an outcome. The risks and unknowns that the venture face at the early stage are enormous. But nevertheless the quality founders take ownership over this responsibility. Although the path forward to achieving the desired outcome is unknown, the founder is fully committed to delivering the 10X outcome anyway.

This taking of ownership is crucial to a startup. It’s what is needed in founders. But that ownership must at least partially be delegated, so it’s also what’s needed in almost every hire, at least early on.

It is easy to detect whether a teammate is taking ownership. In startups the goals that are set are really based upon what the venture needs to have happen, not what seems feasible to achieve. Certain milestones must be hit in order for the startup to survive and advance regardless of whether they seem feasible. So how does a teammate react to taking on such a goal? Do they say “I got it” and they plunge into figuring it out? Or do they start talking about all of the reasons why the goal is really ambitious, and all of the risks that the goal faces? Right away, you can tell who wants to take ownership.

And that’s the key. Some people love the opportunity to have ownership. Perhaps they’ve been working in environments without ownership (e.g. big companies). They have been hungry for some time to really prove themselves, and here, in a start-up, this ownership gives them that chance. That’s who you want.

Ownership is a two-way street, however. In order for a teammate to really be given ownership, they must also be empowered. That means that their responsibility and authority around a given function and set of goals are clear. Many colleagues might be collaborating on this effort. But if this colleague is going to be held accountable for the outcome, they must also be given the authority to drive the outcome.

And then, when someone is properly given ownership and empowerment, they become the ones whose subconscious is wrestling with the challenges of the initiative. They may wake up in the middle of the night as their brain strikes them with the right solution to the problem. The intention here is not to overwhelm colleagues with stress, but instead to spread the burden of ownership around the company so that everyone can strike the right balance: we all can all be challenged and stretched, but not overwhelmed and fried. Too often the founder assumes all of the ownership and they quickly become overwhelmed, while the rest of the team (if the right hires have been made) are feeling dis-empowered.

Hiring

A rule-of-thumb for hiring for a founder or a CEO is to always look to hire people who are way better than you are in their area of expertise. For example, in hiring a CMO, you want someone who is way better at marketing than you are. Thus when they are taking ownership over marketing objectives, it makes sense for them to have authority, as they have the right expertise.

And of course all of that makes sense. But I often have observed—in others and in myself— that in hiring excessive emphasis is placed on professional credentials and not enough placed on personal qualities. Typically this dynamic is driven by investors who demand executives with certain resumes, but who, as investors, rarely understand the inner-workings of a startup. Of course the candidate must satisfy the functional qualifications for the role, but if I’m debating between two candidates that do so, and one is stronger professionally, and the other personally, I would take the personally stronger candidate every time.

Why? Because a startup is a team sport, and the team only succeeds to the extent that it works well together. Specifically when hiring there are three personality attributes that critical to evaluate:

• Ownership. Is this person ready to take ownership over their goals & responsibilities? For all of the reasons discussed above, this is vital.
• Company-first. Is this person always looking to make the decisions that are best for the company? Often times employees will be looking out for themselves or for their teams. Particularly in a start-up, everyone must always be solving for what’s best for the company. That’s how the team wins.
• Trustworthy. There is a great series of books about trust within organizations written by Patrick Lencioni. It’s a big topic, but at its simplest, trustworthiness is what you think it is: Are they honest? Can you rely on their commitments? Do they have integrity? Will they be transparent and vulnerable when necessary? Are they respectful? Teams can’t function without trust.

Thus when hiring it is critical to evaluate for these attributes. Around ownership, it’s best to do the following. First, give them all the necessary background information and context. For a major executive or leader, give them a data room similar to what you provide VCs. Answer all of their questions. Second, make your expectations crystal clear. Tell them before you hire them just what the goals and objectives for the role will be. Then, bring them in and tell them to present their plan. Do they take ownership? Are they excited to take on the challenge and present a compelling plan to do so? Or do they squirm and wiggle around the objectives and the risks?

On the other attributes—company-first and trustworthy—do a first screening where you give them no sense of your expectations and instead ask them what they think is important to a company’s success. Do they talk much about culture, trust or perhaps being company-first? See what their take is on what drives success, and if they don’t pass filter them right there. Then after, again, make expectations crystal clear. Provide extensive documentation around how teammates and leaders are expected to behave around being trustworthy and company-first. How do they react? Are they eager to commit to these values? Then dig in and try to get to know them personally. I would look to get out of the building and would go on 2-3 hour hikes with later-stage candidates. What’s their life story? What are their values? What are your colleagues’ takes on the candidate?

This personal assessment is more intuitive than rational, but the critical criteria are clear: will this person take ownership, will they always prioritize the company, and are they trust-worthy?. A company cannot succeed without these qualities, and the founder cannot delegate without them either.

Delegating & Leading

If the founder has hired the right people, then the founder can truly delegate responsibilities to colleagues. As we discussed, this includes giving ownership over functions and goals to a colleague but also empowering them to have such ownership.

What does this look like? This can be complicated sometimes, because the founder has often been focused on solving the startup’s solution and technology for quite sometime, might know the target industry really well, is likely quite bright and over-achieving, and, for better or for worse, likely spends an unnatural amount of time thinking through the startups challenges. Thus for a given set of issues or questions, the founder might often be the one with the right answers.

So when the founder is delegating, how does it work? When the startup really needs to eat, should the founder them self fish or should they teach the colleague how to fish? Often pressure and urgency are bearing down, and it is hard for the founder to resist jumping in and getting something critical done, even if it is an issue that has been delegated to a colleague.

There’s no perfect guidance for this dynamic. Sometimes the urgency is too much and the founder should and must jump in. But realize that while that helps in the short-term it hurts in the long-term. By stepping in and doing instead of teaching, your colleague is less empowered to own their responsibilities.

As always, make expectations crystal clear. Have goals well documented and discussed. Thus your job as a leader is not to tell the colleague what to do but instead to 1) check in periodically to make sure that goals are on track and 2) act as a sounding board and advisor to help the colleague work though challenges. If the colleague is on track, you should stay clearly in this supportive role. If they colleague is falling behind for an extended period, it should be expected that you might need to assert yourself more directly in the function or initiative.

When delegation and empowerment are working well, you should find yourself in a mode of just asking questions and responding to questions. Only if the colleague asks for guidance do you give it. Otherwise, as you check in with the colleague, you ask. But you rarely make a direct statement around what should be done; instead you support your colleague who’s in charge.

This is true even around initiatives where the founder is involved but the colleague is in charge. Let’s say for example that the colleague is running a project to develop a couple of key manufacturing partnerships. The founder/CEO might have lots of key relationships in the industry and thus needs to be brought in for critical meetings. But even though the founder/CEO is involved, they’re not in charge. The colleague is running the project and they are accountable for its success, including deciding when and how to involve the founder. In this way the colleague is fully empowered, and the founder is fully released from the mental burden of managing the project. Instead they just show up when and where the colleague indicates that they should.

Accountability & Celebration

As has been discussed, goals in a startup are about what’s required for survival and success, not what’s feasible. Colleagues must embrace this challenge and overcome the odds in order to keep the startup progressing and on the path to success.

The founder’s role is to help set these goals and hold the team accountable. If the team responds to a goal by protesting that “there’s no way we can get that done that soon!”, the founder has to calmly explain that the survival of the startup depends on it, and that we must somehow figure out a way to get it done on time. As the team accepts the challenge, the founder must hold them accountable to achieving this improbable objective.

And this happens over and over again in a startup: founders holding colleagues accountable to unlikely goals; founders finding the right people who embrace these challenges and take ownership. In the case where colleagues repeatedly are not achieving their goals, the founder has to take the ultimate step around accountability and terminate the colleague.

So the founder must be a demanding leader, pushing the team to accomplish the improbable. But there’s another responsibility for the founder on the flip side: when the team does hit their goals, the founder must be the cheerleader-in-chief and celebrate those wins. If and when demanding goals are achieved, the founder must acknowledge how ambitious the goals were, recognize the great job that the team has done, and heap the praise upon them.

The dynamic of setting demanding goals and not celebrating the wins will quickly lead to employee attrition. Colleagues will take on challenges if they know that they’ll be recognized for achieving them. That recognition and celebration must come from the founders.

Go to Part IV