Management For Startups Podcast

We all have down days. When you're an individual contributor, this isn't so bad. But when you're a manager, your entire team depends on you. How do you deal with motivational issues when you're hit with an inevitable down day? 

This week we deal with the challenge many makers — programmers, designers, hardware engineers — face when they make the leap to management. How do you wake up in the morning to go to work when you no longer get joy from what you do?  (Inspired from this HN thread).

If you're a middle manager, dealing with your boss is going to be one of the main things that you'll have to learn to do. This week, we'll talk about a fundamental technique that every manager would eventually need to learn: the ability to really understand your boss's true motivations.

One of the implications of the manager's job of 'increasing the output of the team' is to serve as the 'shit shield' for said team. This means protecting them from the natural randomness of events in your organisation, especially when it doesn't affect them directly.  But how much to keep from them, and how much to let them know? What rule should we pick, and stick to? This week, we talk a little about how much protection is too much.

In Kim Scott's 2017 management book Radical Candor, Scott describes a management technique that she attributes to ex-Google manager Russ Laraway, who had to integrate the Doubleclick team post Google acquisition. The technique is called Career Conversations, and Scott and Laraway both propose that it could lead to better employee retention. I read about Career Conversations with some surprise, as by that point, I'd been doing something very similar. This podcast describes my experiences using Laraway's Career Conversations in Vietnam.

We've talked about delegation before on the MFS podcast, but one thing that I've neglected to mention is that it's important to 'explain why' when delegating to subordinates. Explaining 'why' — sometimes called providing context, or communicating executive intent — is important if you want your subordinates to make decisions on your behalf.  This podcast is about how to do it, and how to get context for yourself when you're dealing with a boss who doesn't communicate executive intent.

Process change is a critical yet challenging journey for startups. Team resistance often complicates implementation, making it essential to understand pain points. The discussion introduces two key evaluation lenses—pain and reversibility—helping leaders assess potential changes. A structured approach to change management empowers teams to adapt and thrive, making transformations smoother.

Last week we discussed the dangers of firing too slowly. This week we'll discuss the dangers of the opposite view: that of firing too quickly. In my experience, startup managers who fire too quickly tend to have 'high standards', and they tend to come from performance-oriented organisations. The nature of doing a startup though, work against some of their instincts.  We explore exactly how these differences occur, and what to do about them. 

We've discussed the difficulty of firing bad performers in the past — in the last episode on the Manager Ugh Field, for instance, I illustrated the ugh field with a personal story on the difficulty of firing an underperforming subordinate.  I had to steel myself to fire him, and I mentioned all sorts of negative effects that would happen had I allowed him to stay.  In this episode, we will focus directly on this question: what happens when you allow an underperforming subordinate stay on in your company? Why is this a bad idea? 

Navigating the emotional challenges of management is crucial. The concept of the 'ugh field' highlights how anxiety can hinder tough conversations. Strategies like box breathing and mindful meditation are discussed to help managers overcome these hurdles. Transforming this emotional barrier into a strength is the key takeaway, empowering leaders to tackle difficult situations with confidence.