Mastering people management

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🔗 Jake’s Picks

Must-Read Resources for Founders

🚀 Scaling Startups

• How to grow your team without losing your startup spirit (London Daily News)

🧠 Founder Self-Development & Mental Health

• Is founder wellbeing directly proportional to start-up success? (Entrepreneur)

📈 Productivity Hacks

• These 5 Reddit communities offer the productivity tips you need (Fast Company)

🛠 Tools for Scaling

• No code builder for designing and deploying AI agents in critical workflows (Asana)

💡 Hiring Insights

• The 10 most in-demand tech jobs for 2025 - and how to hire for them  (CIO)

👀 ICYMI

• How social media can accelerate your hiring strategy (Scale Smarter Newsletter)

💼 A foundation built through teams managing teams

There’s a distinct difference between scaling your business and scaling your team.  And the more your company scales, the more the scaling team part becomes apparent.

In the early days, while building the company, people management feels like second nature.  The team is small, the goals are clear, and communication happens seemingly organically.  At this point “headcount” isn’t even a thought.

However, there comes a point in your company’s lifecycle where headcount and people operations almost feels like a daily conversation.  What worked for ten people falls apart at fifty, or one hundred and fifty for that matter.  The conversations shift from saying something in person once to all employees to having to send “communications” just so that your message is received across the company.

The more people that join your company, the more it evolves - which means as a leader, you too will evolve.  How your company grows will have a lot to do with how employees are managed, including the systems you build and the styles you adapt to, not to mention preparing for the inevitable challenges you’ll face with politics and egos.

Your job as the founder is to create the best possible group of people, that you will not only manage, but who will also end up managing future employees below you.

A strong middle layer

As soon as you’re at the point where you can do this, bring on your first manager(s) who can be that buffer between your leadership team and lower level employees.  It’s very common for employees to feel like they can talk to the CEO in smaller startups, which is fine.

But you’ll feel the burn of these continuous interactions when you have to manage multiple teams at once.  Your goal is to have these teams manage themselves by managers who you can rely upon.

Self-repeating culture

Let’s face it, you won’t have time to get direct feedback from everyone in the company.  A core component within your management team is how it reflects and communicates your culture.

• Reinforce company values and traditions with management that can then be passed down to employees - share fun anecdotes with management that you may not typically tell to the whole company to help them see why you started in the first place.

• Have your managers select culture stewards within different departments, essentially employees they believe reflect your company’s culture and uphold its values

• Encourage anonymous surveys across teams - nothing fancy, Google forms without email addresses work well

Inevitable politics

How can you talk about people management and not include politics?  You have to build your management team assuming that they will have to deal with politics, which could will find its way back to you directly.

And this is okay.

The unfortunate part about politics is sometimes you won’t know what to do the first time it happens.  This is why you want to set clear expectations and escalation channels with your teams.

Give your teams a clear answer on when you need to be notified about an issue and when you don’t and this will help start to create an escalation path that employees can feel comfortable about.

The essentials: headcount & budget planning

One of the most important components of managing teams is understanding when you can actually scale them.  Even if you are not good with finances, a simple equation applies here:

You really don’t need anything fancy to figure this out, a simple excel file will be sufficient.

Once you have a sense of who your next hires are going to be and how much cash you’re projecting to have on hand monthly, align hiring to specific revenue numbers.  This way as you’re scaling revenue, you also have a roadmap to scale teams with additional resources.

💪 Leveling up as a manager

It’s not uncommon to be a first time manager while being the founder of a scaling company.  After all, you built this company assuming it was going to grow into something one day - leading people was inevitably going to happen.

As scary as it may be to have the responsibility of employees relying on you to make decisions, this is also your opportunity to learn and grow as an individual from becoming a leader.

There are things you can do to help you along the way as this newfound role reshapes who you are.

Create mini efficiencies

There are days where I’m sure you look at your calendar first thing in the morning and realize you’re not going to have time to get any actual work done during the day.  This is where time blocking comes in handy, as I talked about here.

You want to create dedicated blocks of time throughout your week to do the things a manager would do: scheduled blocks of time to meet with employees, to ensure teams have everything they need to function to the best of their ability, and blocks to focus on company strategy.

At the same time, while you balance not being consumed in all company operations, empower your direct reports to make decisions without needing your approval every time.  Set up rules of engagement so it’s clear where they can move forward autonomously and where they will need your input for decisions.

From managing tasks to inspiring outcomes

A shift will happen where you’ll go from doing the actual work as a founder to hiring enough people to take over that work.  At this point your role as a manager shifts to more of a storyteller, a stronger focus on inspiring the vision, mission, and values across the company so employees feel motivated to do their best work.

If you don’t like speaking in front of large groups or teams, practice your messaging with your family and friends.  Speaking in front of groups becomes easier when you’re able to rhyme off your messaging without having to think too hard about what you want to say.

Observe patterns in team dynamics

Pay attention to recurring challenges - whether conflicts, missed deadlines, or low morale -  and treat them as mirrors for your own growth opportunities.

When you see these patterns, ask yourself, “What does this tell me about what I need to improve?”

Once a pattern is recognized, identify who might be the high performing employees directly connected and without micromanaging, empower them to help rectify what the issue may be.  Again, your goal as a manager and a leader is to direct the action more so than doing the action yourself.

A lot of the work you do as a manager will involve overseeing and observing how employees get their jobs done, how processes are implemented, and just generally how everything works within this entity you have now scaled.

At this point you’re not just building and leading a company, you’re also building yourself to be the leader who will be able to lead the company into its next growth phase.  Tied to this is who you are as an individual.

Practicing things like empathy, self-awareness, and honing in on yours and your employee’s emotional intelligence (EQ) goes a long way in ensuring you appreciate the work your employees do but as well, they appreciate you as a their leader.

🎬 TLDR — Your Actions For The Week:

• Scale Your Team → Define which employees are your culture stewards and give them more autonomy to be leaders

• Scale Yourself → Address a recurring challenge, big or small, and instead of solving it, guide your staff with addressing and solving it and have them manage it moving forward

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