A Letter to Founders: How to Manage your Startup Team

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Dear Founder,

When we met last week, you and your co-founder seemed nervous. It might have been for the hundred-eleventh time this year, but some will agree how daunting it is to speak to a skeptic, a VC, who appears to have all the right reasons to grill you, judge you, and reject your idea. However, you seemed to be more passionate to share about your current struggles as a team, although it took some time for us to reach that level of openness

Questions you had that day were somewhere along the lines of..

When and how how we go about fundraising if we have less than 10 months of runway.

As a VC, what do you think about our current service – the upside and the downside?

Given the context and our milestones so far, should we focus on B2B or B2C? We fear that choosing either will create chaos within the team, leaving us in a state of limbo. We’ve been in the circles for weeks. Any thoughts on this?

However, as we delved deeper into our discussion, our conversation was wrapped up in one simple word, transparency. Kim Scott refers to this concept as Radical Candor.

At the Pool

I suspect the reason why you felt like you were in a limbo is not because you two haven’t been thinking harder enough between focusing your team to build for B2C and B2B. Contrary to your belief, it’s never due to the lack of thoughtful considerations but rather the fear of hurting your co-founder or team members. This fear you have is not because you are an incompetent or a dishonest or an irresponsible founder unworthy of your team. It’s because this fear stems from your deeply ingrained sense of responsibility as a founder. And dare I say, you should have less of it. The problem is that you are being too responsible and having too high of a bar on yourself as the founder.


High view

As is often the case with startup founders, we, founders tend to gravitate towards desiring to see the world and its problems as they truly are. Consequently, you become excessively self-conscious to see your faults as they are and thus set impossibly high standards for yourself as a leader. You may question your own competence wondering,

“How am I more competent than this team member when in fact I don’t even know the basics of SEO or Google Analytics?”

“What if I fail to prove the hypothesis I presented to my team and we run out of money?”

Well, as we discussed that day, these are bound to happen and are inevitable throughout your founder journey.

Without a doubt, you will eventually hire dozens, or if you’re fortunate, even hundreds of individuals who possess extraordinary work ethics and knowledge depths that far exceed your own. There will be numerous instances where your goals and hypotheses will be proven entirely wrong, surpassing the occasions where they prove accurate. As the saying goes, running a startup entails being willing to withstand blows from various angles, delivered by the very people and truths you once held dear, and yet rising each morning with the determination to confront the next wave of setbacks.

Sunrise and waves

So, finding ourselves dropped back into this seemingly endless Guerrilla warfare, what course of action should we take?

I mean, we still have no idea what our next milestones should be. We lack a clear understanding of our target customers’ problems and, consequently, the appropriate solutions. And most importantly, we have no clue how to convey this daunting reality to our team members, especially those who left behind their once-dream jobs and aspirations to join us in this chaos.

Well, back on our feet, we founders should embrace the challenges that lie ahead with nothing other than honesty and humility. Founders need to be open and proactive in facing not only the uncertainties of the market but also the opinions and perspectives of our team members. In the words of Kim Scott, we must embody Radical Candor—the audacity to trust that honesty about our thoughts and feelings is not only the best course of action but the only one.

To help you implement Kim’s framework, I have hand-picked and compiled a list of actionable steps that I found particularly helpful. Here they are in point form:

A Coral

  1. Starting from today, foster a culture of open communication, where team members feel comfortable debating and disagreeing to you.

Having a team that knows how to give an honest advice can long-run. Fostering this culture is the very bedrock of managing a startup. Some immediate tips are,

  • Practice Active Listening: When team members speak, make a conscious effort to listen attentively. Be genuinely interested in their perspectives and ideas.
  • Seek Immediate Feedback: When sharing your thoughts, especially regarding important decisions like a pivot, actively solicit feedback from the team. As a founder and manager, go above and beyond to challenge the stereotype associated with managers we’ve all encountered—the ones who claims to know everything but lacks practical skills, earning them the label “an absolute dick” according to the urban dictionary.
  • Choose Trust Over Respect: Trust is your most valuable asset as a manager. Teams gravitate towards and trust leaders who can openly accept criticism without becoming defensive. Contrary to common belief, listening in silence and proactively seeking feedback will earn you more trust and respect.
  • Set Regular Feedback Sessions: Some companies refer to it as “Fix Week,” a dedicated period where, much like engineers, they spend a day or even an entire week focused on troubleshooting and resolving issues that occurred. Create a safe space where strengths, weaknesses, and areas for improvement can be openly discussed. At 500, we utilize the Stop, Continue, and Start framework, where partners share what actions should be stopped or reduced, what should continue, and what new challenges the other person should take on.


Image Source: Superbeings.ai

  • Speak out Humility and Collaboration: Make it a regular practice to incorporate phrases like “I recognize that I’m not the expert in this area, so I genuinely value your advice” or “In order to improve our efficiency, what actions should I start or stop doing?” into your daily conversations.
  1. Lead by Example. Engage in open debates and disagreements with fellow leaders in the presence of the team.

However, note that this approach may not be suitable for the entire team just yet. Practicing yourself amongst co-founders will set the standard for future debates and disagreements that others will follow.

  • This practice will prove particularly beneficial as your team grows to over 30 individuals. It can be time-consuming and repetitive to listen to disagreements or feedbacks from each team member individually. Implant a culture of open debate and disagreement among leaders and it will expedite the process and save valuable time.
  1. Remember the Six-Second Rule. Train how you react to the feeling of discomfort when hearing or waiting for a criticism

In the initial weeks, not all members of your team will be familiar with how or when to share their thoughts. However, it is essential not to let the fear of discomfort hinder your efforts to cultivate this valuable culture.

  • During the first couple of weeks, not all members of your team will know how or where to the draw the line when criticizing. But don’t let that fear of discomfort stop you from fostering this valuable culture.
  • When asked to criticize or disagree, team members might initially respond saying, “Everything seems good so far” or “Thanks for asking, but I don’t have any feedback yet.” However, don’t be so quick to compromise. Take a brief pause, count to six, and allow the silence to sink in. Demonstrate genuine interest and patience in hearing their perspectives. Once they feel ready, ask again for their honest opinions.
  1. Rather Share Too much. Be completely open about the challenges and uncertainties the company faces, as well as your personal struggles as a founder. Your team needs to hear the truth, and you need their support.

Remember that avoiding discussions or attempting to hide faults will not resolve the issues. Instead, confront the problems head-on and accept failure as a part of the journey. From there, you can pick up the pieces and move forward.

  • The longer you take to break the news, the harder it will be for your team to adapt and the deeper the feeling of betrayal.
  • Remember that avoiding discussions or attempting to hide faults will not resolve the issues. Instead, confront the problems head-on and accept failure as a part of the journey. From there, you can pick up the pieces and move forward.
  • Remember that we as early-stage startups, we fail forward to succeed.
  • Show Vulnerability and Mistakes: Lead by example and be open about your own vulnerabilities and mistakes. Encourage a learning culture where failures are seen as opportunities for growth and improvement.
  • Yes, all this won’t change the fact that the coming times will be tough, so set clear expectations. Clearly communicate your expectations to your co-founder and team members regarding goals, performance, and responsibilities. Ensure everyone understands their roles and what is expected of them.
  1. Do not cancel or postpone your 1:1 meeting with your team. Show that you care.

The way founders allocate their time reflects their priorities.

  • Consistently postponing or canceling 1:1 meetings sends a message to team members that they are not your top priority.
  • After deriving action items from your 1:1 meetings, proactively schedule the next meeting to discuss how things have progressed. By doing so, you reinforce your commitment to the growth and development of your team.

So, here is my letter to you, expressing my well wishes for you and your team until we meet again.

– Peter

  1. I think your team should consider focusing on the B2B side as a potential avenue for growth.

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