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Product Management

Three product leaders to learn from at #mtpcon inside Pendomonium

Shaw has 10+ years of product management experience, having worked at pre-seed, venture funded, corporate funded, and Fortune 500 companies. Most recently, he led product at HavenLife, an insurtech startup in NYC. 

Subscribe to his weekly newsletter: The Elements of Product Management @ <a href="https://shawli.substack.com/">shawli.substack.com</a>

Shaw Li

<p>Product managers who have never worked with founders often find their first experience a bit jarring. “f**ked” and “crazy” have definitely been thrown around. But “crazy” is a label we use when we don’t understand. What makes working with founders challenging and different from other executives?</p>
<h2>What do founders do?</h2>
<p>Founders at early stage startups have three important roles: individual executor, people manager, and visionary. How much time a founder spends in each role will vary depending on the founder’s preference, the founder’s skills, and the company stage or needs.</p>
<ul>
<li><span style="font-weight: bold;">Founder as Executor &#8211; </span>In this role, the founder is using her or his specialized knowledge or skill.  Perhaps the founder previously worked as an industrial designer of medical devices or sales representatives cold calling potential customers. By using skills and gained experiences, the founder acts as an individual contributor, a “doer”, responsible for completing tactical tasks (e.g., creating designs, draft business terms).</li>
</ul>
<ul>
<li><span style="font-weight: bold;">Founder as Manager &#8211; </span>In this role, the founder is a people manager, responsible for managing others.   Recruiting and hiring are top of mind as are coaching, retaining, and firing. The role’s focus is on assembling a group of people working together to support the business.</li>
</ul>
<ul>
<li><span style="font-weight: bold;">Founder as Visionary &#8211; </span>In this role, the founder is responsible for setting the company’s vision, mission (i.e., purpose) and goals (i.e., shorter term objectives to reach the vision). As the visionary, the founder is constantly evangelising, painting a picture of the future to convince people why reaching this vision is worthwhile.</li>
</ul>
<p>Each of these roles are dynamic. A founder will jump among these roles throughout the day, even from moment to moment during the meeting. That’s why many founders describe their day as a whirlwind of activities because it will literally feel different playing a new role. Being aware of this dynamic is the starting point to improving your working relationship with your founder.</p>
<h2>Is there a difference between startup founders and other executives?</h2>
<p>Founders frequently hold executive positions (e.g., CEO, COO, CPO, CTO), but there are differences between a founder and executive and other non-founder executives.</p>
<h3>Founder’s have more control, both formally and informally</h3>
<p>Generally, founders own more shares of the company than other executives, giving them more control over the direction of the company. They may overrule decisions by other executives. Besides control through ownership, founders usually have amassed large informal control through influence and relationship with key employees, advisors, and investors. The combination of hard and soft power give the founder’s opinion a larger weight than other executives.</p>
<h3>Founders are motivated differently than non-founders</h3>
<p>Founders are motivated primarily by financial gain and control whereas other executives are more motivated by stability, prestige, affiliation, and recognition. This isn’t to say other executives aren’t motivated by financial gain or control, but to a lesser degree.</p>
<h3>“It’s my baby!”</h3>
<p>For example</p>
<blockquote><p>At Blogger, [Evan Williams] consistently made control decisions rather than wealth ones. [&#8230;] He also refused an acquisition offer that threatened his control of the startup, even though that refusal meant losing his entire staff.<br />
<em>&#8211; The Founder’s Dilemma by Noam Wasserman</em></p></blockquote>
<p>Non-founder executives generally aren’t willing to make the same trade-off because they can exchange their skills for comparable compensation and level of control at other companies. Founders, once they are hired by someone else, have to give up that control.</p>
<h3>Above average risk taking</h3>
<blockquote><p>More than 90% of startups fail.<br />
<em>&#8211; Startup Genome Report Extra on Premature Scaling</em></p></blockquote>
<p>You’re more likely to do well in life if you get a job working at Google. But founders are all willing risk takers, trying to beat the odds. That mentality is different than other executives who are hired and join the company and that risk taking mentality will influence their decision-making.</p>
<h2>Advice for product managers working with founders</h2>
<p>First &amp; foremost, <span style="font-weight: bold;">help your founder become consciously aware of the three simultaneous roles they’re playing</span>. The working life of a founder can feel like being inside a tornado, swirling from one topic/decision to the next. This often requires the founder to switch roles: executor one minute, visionary the next. When you observe these, point out the change in setting and context. If you’re running the meeting, set the context before going into the details. Bringing awareness will help the founder define what’s being asked of her or him.</p>
<h3>Determine the founder’s default role</h3>
<p>All founders gravitate towards one of the three roles: executor, people manager, or visionary. It’s what they excel at the most and what they fall back upon when stressed. Knowing the founder’s default role will help you determine how best to complement the founder as a PM. Discuss with your founder what they gravitate towards. Here are some possible identifying traits:</p>
<ul>
<li><span style="font-weight: bold;">Executor founders</span> have practical skills or knowledge and like to get into the tactics. They usually have worked for several years as an individual contributor (e.g., software engineer, industrial design, customer service representative, baker, etc.). On their good day, they are masters of their craft. When overdone, they get stuck in the weeds or become perfectionists.</li>
<li><span style="font-weight: bold;">People manager founders</span> have a strong EQ. They understand what drives and motivates people. Organizing communities and connecting people come naturally. People energize them. On their good days, they are teachers, connectors, guidance counselors. When overdone, they become micromanagers and dictators.</li>
<li><span style="font-weight: bold;">Visionary founders like ideas and thinking.</span> They generally dislike some aspect of the status quo. Doing and people are not the focus. It’s about the future. On their good days, they are dreamers, evangelists, motivators. When other days, they become disconnected from realities, any limitations or practical constraints.</li>
</ul>
<figure id="attachment_22456" aria-describedby="caption-attachment-22456" style="width: 1024px" class="wp-caption aligncenter"><img loading="lazy" decoding="async" class="size-large wp-image-22456" src="//wp-content/uploads/2020/12/matus-kovacovsky-eIvLuyDjCQI-unsplash-1024x683.jpg" alt="Photo by Matúš Kovačovský on Unsplash" width="1024" height="683" srcset="/wp-content/uploads/2020/12/matus-kovacovsky-eIvLuyDjCQI-unsplash-1024x683.jpg 1024w, /wp-content/uploads/2020/12/matus-kovacovsky-eIvLuyDjCQI-unsplash-300x200.jpg 300w, /wp-content/uploads/2020/12/matus-kovacovsky-eIvLuyDjCQI-unsplash-768x512.jpg 768w, /wp-content/uploads/2020/12/matus-kovacovsky-eIvLuyDjCQI-unsplash.jpg 1920w" sizes="(max-width: 1024px) 100vw, 1024px" /><figcaption id="caption-attachment-22456" class="wp-caption-text">Photo by Matúš Kovačovský on Unsplash</figcaption></figure>
<h3>Become the executor when working with visionary founders</h3>
<p>This type of founder is often not aware or concerned with the challenges of execution. They may not know how to tactically execute to achieve their vision. PMs can help by:</p>
<ul>
<li>Bring in some processes (e.g., checklist, document procedure, organization), but give some slack when some of those same processes get broken or bended. Use an 80/20 rule. Pick the processes that you really want to fight hard upon and hold your ground, but allow some areas of spillage.</li>
<li>Give them dedicated time to dream. Maybe that’s with documenting the company or team’s mission statement. Perhaps it’s time set aside for “blue sky” brainstorming exercises. Create a space, but also mark when it isn’t the right time (e.g., final contract negotiations).</li>
<li>Bring them the facts to ground them to reality, but seek guidance for tactical decisions from someone else. Junior PMs often want to treat visionary founders as expert PMs. That’s a recipe for disaster because a visionary founder is not a tactical execution expert. Instead, use them and their vision to build a network to consult with.</li>
</ul>
<h3>Create co-creator situations with you executor founders</h3>
<p>A “doer” likes to do, so create a way to co-create in a structured manner. Discuss with the founder how, when, and where they want to get involved and with what project/initiative. This conversation is especially important as product(s) grow in complexity because a “doer” won’t have the time or mental capacity to be involved in everything. Some specific examples of how to create structure:</p>
<ul>
<li>Invite them to sit in on customer interviews. Make sure the founder speaks last if you’re discussing interview learnings.</li>
<li>Identify a less time-critical project, where they can be involved as an individual team member from beginning to end.</li>
<li>More frequent check-ins throughout the creation process, not just at the end. In these check-ins, assign work (tasks), that the founder has to utilize his expertise. Don’t just present and take feedback, but tell the founder you’re incorporating her or him into the project team.</li>
<li>Ask her or him to teach you a specific skill or technique. Use their expert knowledge. Many executor founders enjoy demonstrating their expertise.</li>
</ul>
<h3>Bring conflict resolution techniques to people manager founders</h3>
<p>Making everyone happy is impossible. People manager founders will struggle keeping everyone at the company content. Thus, they may delay resolving open conflicts or take actions that minimize creating conflict. A great group of people don’t necessarily create a great product. Introduce healthy conflicts resolutions techniques (e.g., define a time, give everyone the opportunity to take turns talking and listening, remind people that everyone is working at the same company). Junior product managers often fall into the trap of being too focused on the decision and rationale of an issue without considering the impact on employee’s at the company.</p>
<h3>Make sure your strengths complement your founder’s default role</h3>
<p>Sometimes, your skills and interests directly oppose a founder’s. For example, I’ve seen product managers try to push for a competing vision contrary to the founder’s vision and lose to a visionary founder. Very few founders are going to cede control to their default role. If your skills don’t compliment your founder’s default, your job will eventually be in jeopardy.</p>
<h3>Change your style as the founder grows and changes</h3>
<p>All successful companies that grow, changes are inevitable. Those changes will also force your founder to change, where their default role may no longer be the same as before. You can only observe this over the long-run, typically 1 &#8211; 2 years. If you identify the change, re-evaluate yourself. Do your skills still complement your founder? Are you also growing and changing to adapt the needs of your founder?</p>
<h3>Don’t assume your founder is your product mentor</h3>
<p>There are many things you’ll learn working at a startup, but junior product managers sometimes mistakenly treat their founder as their product mentor. This is frequently the case if there aren’t any other senior product leaders at the company. But a founder, even if she is your manager, isn’t always also an expert in product management. Even if the person is an expert, the founder may not have the time dedicated to be your product mentor. That’s why I encourage all product managers to develop product mentorship outside of their company via meetups, conferences, twitter.</p>
<p>Through some understanding of the founder’s role and adjustment of how you work, you’re more likely to succeed in building a complementary relationship with your founder and help build a great product.</p>
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