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Making the difficult decisions easier

People pleasers, this one’s for you! (Also me. Because we’re always a work in progress.)

Think back to the last time you had a difficult decision to make that impacted others. No, not what you were going to eat for dinner last night. (That’s a different kind of difficult decision.)

I’m talking about those decisions that can make or break someone’s day. You choose whether or not someone should be promoted. You reprimand someone. You choose whether or not you want to approve the budget for a nice-to-have but not a must-have. You choose who will be working on a specific project, or perhaps you need to change who is actively working on this project.

All decisions have consequences – some more than others. As managers, we face these decisions every day, and we also face the consequences these decisions bring. The most difficult ones are the ones that make at least one person unhappy, which is why I called out the people pleasers of the world at the beginning of this.

One of the most challenging things I have learned over time as a manager is how to sit with and respond to a direct report or peer (or your boss) not being pleased with the decision I made. My default move is to rush towards a solution that makes everyone happy, even if it makes my life more difficult.

Here’s the thing. If you know you’re a people pleaser and you know you struggle with people not liking you, this is really, really important for you. Reflect back on the past 3 months of your work and make a list of the difficult decisions you’ve had to make, and list the outcome of these decisions. If everyone was happy 100% of the time with the decisions you made, I want you to raise a little warning flag in the back of your head and ask yourself, “Did I make these decisions because they were the right decisions, or did I make these decisions because I was avoiding having someone be unhappy with me?”

Now, this isn’t to say that if you make a decision and everyone’s happy that you’re immediately doing something wrong. Everyone loves free pizza, after all. But it’s healthy to reflect back on your decision-making and see if you (1) avoided making a difficult decision, (2) walked back on the decision you made because someone was unhappy, or (3) apologized for making a decision that didn’t warrant an apology.

I know I titled this “Making difficult decisions easier”, but I suppose it’s a bit of a misnomer. Like with many things, making difficult decisions and dealing with the aftermath of these decisions will only get easier with time. It’s not a bad thing to feel bad when people are upset with your decision - it means you care, and that’s healthy. But too much of this can be detrimental to you, and your organization’s productivity. This is a muscle you need to build over time, especially if you’re more naturally inclined to shy away from having people dislike you. Welcome to management, and welcome to life. :)

What I’m reading

I finished Measure What Matters at the end of January and I highly, highly, highly recommend it. Here’s my full review for it:

Title: Measure What Matters

Author: John Doerr

Good for: Managers, leads, basically everyone - but particularly those who either work in an environment that uses OKRs or have the ability to introduce OKRs into their team/org

Summary: Measure What Matters breaks down OKRs (objectives and key results) and gives you concrete examples of how other organizations have used them in the past. Created by Andy Grove at Intel, OKRs have since powered the minds and operations of corporations, non-profits, and more – most notably Google.

Why I recommend it: If you work in an environment that currently uses OKRs or you’re interested in introducing a more objective, measurable way to track and measure success in your organization, this book is gold. It’s a quick read and alternates between informational sections and real-life examples to keep you focused and retaining the information.

I also finished my annual re-listen of Atomic Habits. I love starting off my year with a mental reset around my habits, and Atomic Habits is exactly what I need.

Now I’m reading High Output Management since I have this Andy Grove focus. It’s my selected business book for the month of February, and I’m determined to actually get through it. (I finally got through the Breakfast Factory, so this is the best I’ve done to date.)

Check out the full book list for recommendations and an ever-growing reading list.

Note: Links to books in this section are affiliate links to help support the purchase of the rest of my books :)

What I’m working on

I’ve been wrapping up a number of projects - our SOC2 Type 2 audit, headcount planning, our plans for worldwide domination… and now I’m focused on writing a lot of process documents so when I inevitably hire a lot of people this year (yay!), we have really solid procedures in place to make the hiring and onboarding process seamless for both our newcomers and existing team members.

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