How to understand what your boss is thinking

Picture of Matthew Stibbe
Posted by Matthew Stibbe

There are a lots of articles about how to impress a boss. This isn’t one of them. This article is about how to understand what your boss is thinking.

I’ve been a boss for 25 years and I wanted to share my own experiences. I want to show you what the world looks like from my side of the table and maybe explain what your boss is thinking about.

Being a boss is an exercise in reconciling different, apparently contradictory, ways of thinking. Montaigne put it best:

Anyone who turns his prime attention on to himself will hardly ever find himself in the same state twice. I give my soul this face or that, depending upon which side I lay it down on. I speak about myself in diverse ways: that is because I look at myself in diverse ways. Every sort of contradiction can be found in me, depending upon some twist or attribute: timid, insolent; chaste, lecherous; talkative, taciturn; tough, sickly; clever, dull; brooding, affable; lying, truthful; learned, ignorant; generous, miserly and then prodigal — I can see something of all that in myself, depending on how I gyrate.

I have identified four contradictions that sum up my experience as a boss:

  • Passion vs anxiety
  • Order vs chaos
  • Geek vs creative
  • Manager vs entrepreneur

In each section, I’ve tried to say how I feel and then explain what that means for colleagues. I’d love to hear your experiences and feedback.

Passion vs anxiety

Brian Blessed in Flash Gordon - 'Diiiive' Woody Allen looking anxious
Half the time I feel excited, energised and ambitious. I want to charge ahead and get stuff done, regardless of the risks. ‘Who wants to live for ever? The other half of the time, I’m looking over my shoulder, worrying about what might go wrong and stressing about something. ‘Only the paranoid survive’.

Willing, judging and acting

For my colleagues, this means:

  • There’s a period where my enthusiasm precedes an actual decision. That’s a good time for input. But once a decision has been made, DIIIIVE!!!!
  • Contrary to popular opinion, I’m not everywhere and I don’t know everything. Take responsibility. Communicate. Clean as you cook.
  • You can help me by reducing risk and spotting issues before they become serious problems. Speak up if you spot something going wrong.
  • If I’m distracted or not responding promptly, try to remember that I have other plates spinning. Sometimes, you might have to pick your moment.
  • Be big and bold yourself. Propose solutions, have ideas, get excited, and commit passionately to something. I like that. I can totally relate.
  • I’m more excited about starting a project than finishing it. If you can be the person that loves finishing something beautifully, we’ll get on well.
  • Conversely, I’m a neurotic completer-finisher of small tasks. If you can break down a big thing into little jobs for me to do, I’ll go at them like a dog to a bone.

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Building a minimum viable bureaucracy

Two boxes of matches, one tidy one chaotic

Too much chaos prevents action, confuses people and produces inconsistent, unexpected results. Too much order stultifies the brain and makes people and companies brittle; what Churchill called the ‘dead hand of inanition’.

There is an optimum balance between the two that allows for change but also gives people enough consistency that they can do most of their work without having to constantly reinvent the wheel.

So what I aim for is a ‘minimum viable bureaucracy’ – enough process to keep things rolling smoothly but not so much that it gets in the way.

People are 70 per cent water, but we appear solid. Similarly, businesses are 70 per cent chaos but from the outside, they look like a solid collection of rules, processes and systems. Understanding this makes it easier to see how the business looks to an owner.

Balancing chaos and structure

As an entrepreneur, I lean towards being chaotic. I’m comfortable with risk, uncertainty and certain kinds of cognitive dissonance. But as a manager and a geek (see below) I like familiar routines and setting up shortcuts and hacks that make things more efficient. With this in mind, you can work well with me by:

  • Being wary of creating more bureaucracy than necessary.
  • Not adding to the chaos unnecessarily.
  • Improvising sometimes. I’ll hum it, you sing it.
  • Telling me when you’re uncomfortable with too much chaos or too much structure.
  • Accepting that sometimes I don’t always know what’s going to happen. And that, secretly, I like a bit of creative chaos.
  • Understanding that fighting chaos is hard work; it’s easier for you to say ‘this is a mess’ than for me, as a boss, to straighten it out.
  • Working with me to make sure that the processes we do use to straighten out the mess are fit for the job.
  • Refactoring processes regularly so they don’t outlive their usefulness.

Geeking out vs Creativity

In the last couple of years, I realised that I am a deeply creative person but that my creativity expresses itself through business – inventing new systems, exploring new opportunities, working with colleagues and so on.

The things that matter to me as a creative person are (mostly) the same as the things that matter to artists, authors and actors. They relate to self-expression, development and the dizziness of making something new and good.

I wrote about geeks and creatives before, but only today applied the whole matrix to myself, rather than just the geek half. And, of course, I’m a geek. I used to make games for LEGO, for heaven’s sake. You can’t get geekier than that.

So here’s a table that expresses both sides of my boss-personality.

  I’m a geek I’m a creative person
I ask How? Why?
Respect from Peers Audience
My life is Deterministic Opportunistic
Decisions made on Data Instinct
I’m driven by Obsession Passion
My narrative Flowchart Story
Care about The future The moment
Need Feedback Praise
Rely on Logic Emotion
I say Look at this Look at me
Thinking Linear Circular
Logic Finite state Infinite possibilities
Measure Deliverables Impact

Combining geekiness and creativity

So, what does this mean for my colleagues?

  • The best results happen when both modes are fully engaged.
  • Try to understand whether I’m geeking out about something (obsessional detail focus) or getting creative (lofty, blue sky big ideas) and react accordingly.
  • The appropriate response may be in the other direction; for example, you can ground creative ideas with geeky logic.
  • If you wait long enough, I’ll probably flip from one mode to another.
  • Creative ideas tend to take longer to come to fruition – they’re waiting for some geeky implementation. Sometimes, like a stray balloon, they just float away.
  • The flip side is that it’s easy for me to get lost down the rabbit hole of some geeky implementation detail. Don’t let me do that. A new app or gadget isn’t always the right solution.
  • If you’re dealing with my geek side, The Nerd Handbook is essential reading.

Manager vs Entrepreneur

Actors being a PC and a Mac from the old TV advert

I’m both a manager and an entrepreneur. I love starting and building a business. Like second marriages, being an entrepreneur is a triumph of optimism over experience. But I’m also a manager. I love to help my colleagues, coordinate activity, create systems and all that good business-building stuff.

  I’m a manager I’m an entrepreneur
Wants To be somebody To do something
Favourite app Excel PowerPoint
Values Consistency Spontaneity
Role model Orchestra conductor Jazz pianist
Relies on Brains Guts
Studies Metrics Results
Suffers from Status anxiety Cash flow anxiety
Studies Machiavelli John Boyd
Core strategy Evolution Revolution
Writes Reports Blog posts
Business hero Jack Welch Richard Branson
Works A 96-hour week A 96-hour week

Trying to be a good manager

The manager’s rewards are small, discrete but frequent while an entrepreneur’s rewards take time and sometimes never come. Being an entrepreneur is not all private jets and supermodels. Only five per cent of startups have more than five employees on their tenth anniversary. Being an entrepreneur is risky: everyone wants to go to heaven, but nobody wants to die.

Being a manager isn’t about power. Managers aren’t the boss of you even if they sometimes have to prioritise your work or coach you. Management is a role, like a writer or driver. It’s a thing you do, not a position in the hierarchy, at least at Turbine and its parent company Articulate. I want to avoid power politics, and I don’t want to be a bossy boss. I prefer the servant-leadership philosophy.

Trying to understand how people think

But when it comes to being an entrepreneur, I’m going to admit something to you that I have felt for 25+ years but never told anyone: I simply don’t understand how employees think. My behaviour is so conditioned by my experience as an entrepreneur and manager that it takes a huge imaginative effort to put myself in their shoes. It’s like Sheldon Cooper trying to figure out a dirty joke. This is a big weakness on my part, but the chances are that other lifelong bosses will have the same feelings.

Like me, they will probably compensate by over-communicating. They think that if you can understand them and their intentions better, your behaviour will automagically align with their expectations. This might happen but you can help them a lot by over-communicating back so that they understand your thinking, needs and expectations too.

In fact, the best way to manage your boss is to find smart ways to communicate with them. Write a blog post. Send an email. Buy them a drink. Have a chat. Schedule a brainstorm. Ask for a problem to solve. Read about great managers and entrepreneurs and share your findings. Take heart. Your boss is human too.

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