Part III of this guide reviewed how to organize concerns and objectives across the team, so that company performance is optimized and the founder shifts their efforts more towards leadership than personal superhuman productivity. Here in Part IV we’ll talk about organizing concerns temporarily: not everything has to be dealt with at once, thus what sort of system organizes issues in time?
We’ll also get into the inverse of the dynamic we’ve been discussing: instead of taking on too many responsibilities, sometimes founders can ignore responsibilities, and this is damaging to both the business and the founder’s mental health. Then to wrap up, we’ll review how you might put the principles of this guide into practice.
We’ve talked about organizing the issues and challenges of the business by delegating to and empowering different colleagues, i.e. organizing through the org chart. But there is also the need to properly organize temporally.
Most founders are hyper-concerned about their startup. Every last issue, every last detail that seems off they will feel compelled to address. And generally that’s a good thing: this commitment to the company is critical to the company’s success.
But as the company progresses and becomes more complex, the set of issues and concerns that they founder identifies becomes overwhelming. They must develop a system in order to effectively address the concerns and not have them rattling around their brain, generating distress.
There is an entire body of literature around best practices for organizing a company, whether it be through sprints, OKRs, quarterly reviews, etc. This corpus already explains the practices well and such practices are beyond the scope of this essay (to me the best summary of these practices is Traction).
However you organize your company, it should include:
With such a framework, you have places to put questions and concerns as they come up. A question about how your marketing is going? Put it on the agenda for your next 1:1 with your CMO. An idea for a big strategic shift? Write up the thought, and put it on the agenda for your next quarterly strategy meeting.
When a concern comes up, if it is truly an urgent fire, you of course have to address it right away. However many such issues aren’t that urgent, but you must have a way to process them. Document them in the agenda or backlog of the appropriate check-point in your cadence and system. That way, you will not carry them around in your subconscious as another distraction, nor will you disrupt your team by prematurely pulling them in.
When you do address the issues with your team, be sure to clearly document the outcome or decision. So let’s say you raised that issue with your CMO at the next 1:1, and they said that they feel that there’s a need for some new web pages to better convey the messaging, and that they’ll have that tackled over the next two sprints. Document that decision, and document a reminder to yourself to check in on the pages in two sprints time. That way, again, the issue is processed, and you don’t need to be troubled by it. You have a system and a cadence and documentation that will enable you to monitor the issue when the time is right.
We’ve talked about how it’s important for the good of the company and of the founder to organize concerns, shrink the scope of concerns, and schedule time for concerns. But while it is important for the founder to thus manage concerns, it is also important to confront concerns, particularly the critical ones that the founder is responsible for. We don’t want excessive concerns and fears swirling around in the founder’s head, but we also don’t want concerns to be haunting the founder—and the business—because they are not being confronted and addressed.
Of course at the top of the list is addressing problems inherent to the business or its product and technology. Delusional founders pose great risk both to their startups and to their own mental health. Founders who try to ignore or evade the truth around their company’s challenges will quickly encounter failure for the business as well as severe psychological angst. Unaddressed challenges will fester in the founder’s mind and generate compounding anxiety and fear. Instead founders need to be fully committed to the truth: the truth of their product, their customers, their financials, and of all aspects of their business.
More challenging are the problems that founders are not aware of. The best mechanism to identify them is the rest of the team, but the team will only be forthcoming about the problems if the culture encourages such candor. This is again where trust is so important. Is the founder trust worthy? Do they create a safe space for telling the truth, even if it's bad news? If so, is the colleague trustworthy? Is their impulse to candidly identify problems, even if they are in their own sphere of responsibility (and they might fear blame)? Without developing the right culture of trust, the founder may never become aware of such problems before it’s too late.
Many of the most difficult problems facing a startup and a founder, however, are about people. These are challenging because while teams are composed of professionals they are also composed of human beings with complex emotions. Furthermore, the team’s humanity is stressed by the extraordinary pressures in a startup. As a result personnel issues can be tricky to navigate and have the potential for explosive and distressing consequences. Because of this founders can tend to ignore or only half address personnel issues. But a startup's progress is a function of both each individual’s performance as well as the quality of the collaboration between individuals. Thus personnel issues are critical threats to the company and must be addressed by the founder.
The key capability involved is the willingness to have challenging, uncomfortable conversations with colleagues and address the issues head on: “You’ve missed your key metrics for the last two quarters by 20%. Let’s talk about what’s happening and how we can get to success.” “A number of colleagues have brought up issues about working with you. Their feedback is documented here. I’d like to talk to you about it and see how we can get to a better situation.”
There are three critical attributes to bring to these conversations. The first is to keep your emotions in check and remain calm. The second is to be professional in your diction: even if your demeanor is serene, you need to avoid language that can be overly critical, disrespectful or passive aggressive. Cite facts and previously documented agreements; avoid speculation or subjective judgement. Lastly and most importantly: everything in these conversations should be focused upon what’s best for the business. Nothing should be personal: about the colleague, their teammates, or yourself. Always the objective is to solve problems in a way that is best for the business.
Founders must hold their colleagues accountable to goals and to standards of collaboration. When the colleague comes up short, the issues must be addressed. At first the founder should strive to support the colleague in developing plans for improved performance. Expectations around improvement—whether it be metrics, deliverables, behavior, etc.—should be made as clear as possible and be documented so that the colleague has a total understanding of what the desired state is. If the colleague makes progress, the founder should recognize and cheer the progress. Oftentimes founders and leaders can unlock new levels of performance from colleagues with the right candid coaching.
But sometimes a colleague proves to be just not the right fit. Goals continue to be missed. Interpersonal issues persist. The amount of time the founder must spend coaching and setting expectations becomes overwhelming. Here too the founder must confront reality and look to find a replacement and terminate the problematic teammate. Such episodes are difficult, disruptive and time-consuming. Decisions, however, should always be about what’s best for the business, and when a colleague becomes too problematic, the founder must be willing to pull the plug.
Startup founders face enormous challenges. The probability of success for their venture is quite low. And given the experience of most founders, the probability of enjoying quality mental health as a founder is low as well.
However the founder does not have to resign themselves to these low odds. As this essay has conveyed, there are a number of practices that a founder can employ to manage their mental health. The practices range from focusing on personal psychology to focusing on startup leadership. As has been discussed, better leadership drives better mental health. And better mental health drives improved leadership, which in turn ramps the chances of the startup’s success.
Where to start? There are too many approaches to employ to do them all. Start with what seems appealing to you. But make the effort deliberate. Document what you plan to work on and the approach that you intend to take. Have a cadence whereby you’ll revisit the effort and check in on progress. Make note of whether it is driving the intended impact.
Through such a deliberate approach, you’ll learn about how you’re learning and growing. In this way you’ll find what approaches best work for you.
So get started however works best for you, but be sure to get started. And do so early.
I’ve worked with founders who right out of the gates in the first year of their startup begin to experience heavy mental health (and leadership) challenges. Some will say “well I’m guessing that this is hard at the start but once we get up and rolling I’m sure that this will dissipate.”
Unfortunately, the reverse is true. As a startup grows it becomes exponentially more complex: more customers, more employees, more partners. All of this complexity drives more challenges for the business and can generate more anxiety and leadership pitfalls for the founder.
The difficulties, however, can be abated if you get on it early. Develop mental health practices in order to build your resiliency to hard moments. Work on your leadership techniques and team structure and culture so that as you grow, your growing team can become more and more successful and can take on the new hurdles at your next stage.
I had a Board Member and Advisor who was a collegiate athlete before becoming a successful founder. And she used to explain to me that intense, world-class athletes don’t just lace up their shoes and run a marathon or throw on the swim cap and crank out a 1500m freestyle race. Instead of course they prepare for these extremely challenging endeavors through holistic training.
Founding and leading a startup is in many ways just as challenging an undertaking as a marathon or triathlon … except that it goes on non-stop for years! But the difference is that founders by and large go into their endeavor with little deliberate training and work on how to endure and overcome the challenges. Such an approach is madness and results in the struggles so common to founders.
But don’t let that be you. Instead proactively take on the challenge of being a founder. Specifically: address the intertwined issues of mental health and leadership in order to give yourself the best shot at success, both professionally and personally.