The skill that gets you fired or promoted: managing up

How to not reach your "oh shit" moment or.. how to get ahead of 90% of your peers. Yeah, really.

I'm writing this article on the back of a frustration that happened last week and many times over the past year:

• I have a problem on my list today because someone else (whom I pay) promised me something weeks ago and didn’t warn me that they couldn’t deliver in time. I’m out of options and time.

I want to talk about this in very clear terms in a way that I’m missing from most books and articles. “Managing up” or more importantly, being reliable, is not just one of many skills that you need to get right. It is the one.

It’s a tablestake that can be the sole reason why you fail or succeed in your career. It’s not sexy, but it's vital. And so many people across all levels still get it wrong and land in serious trouble.

Every manager is talking about this when they say, “Hiring good people is hard.” It’s hard to find those that are reliable.

Some of us get in trouble more often than not because we like saying “on it, boss” a little too fast. We want an advance on this recognition and pay the bill later.

“Can I have an advance on that recognition, please?”

Let’s map it out.

“S*** rolls downhill”

Some people understand the phrase “S*** rolls downhill” as a stand-in for how some leaders deflect blame downwards. You hear it often when colleagues get together and talk about the latest company gossip because someone else got in trouble.

Sometimes, I have more context about what “actually” happened, especially when you are part of a leadership team. And more often than not it’s about reliability.

Managers talk to each other. Especially when they land in hot situations because of their line reports. Whether you like it or not, that’s a reality.

Every other line manager I've ever met hates chasing their line reports about stuff. This behavior usually indicates that trust is not there (yet) that things will get executed without someone checking in. It can also be a sign of a micro-manager that has a control fetish. In either case, trust is earned even with those:

There is a type of person that always delivers the best slides, the best reports, but they suck in holding deadlines. Chasing people is an antidote to that, but not one that you want to be at the end of.

Things always go wrong, and we will be wrong about our initial estimations of when things are done all the time. But if you promise something by Tuesday, and your manager really expects it the next day and asks you on Monday - because they committed that deadline to someone else higher up themselves - and your answer is "Oups. Sorry, it will be next week; we had too much work." You just placed yourself in trouble:

I hear this scenario in different variations constantly, and most people I coach tell me, "Yeah, but we couldn't hold the deadline because of A, B, or C; it's not my fault!"

And I always tell them the same:

"You were not warning your manager/peer that you could not hold the delivery when you could have earlier. You make them look unreliable towards their manager, and they will trust you less now.”

You leave the person you committed something towards without options. Doing this consistently is an expressway to a lack of trust and, in the worst case, getting fired.

I’m not hyperbolic about this; I’ve seen it happen with juniors and senior leaders. In the C-Suite, you might not be a direct report to someone except the CEO, but if you keep putting others into bad situations, it will accumulate where it really shouldn’t.

It’s about timing, not fault.

I've seen mentees get fired over this, and they are perplexed about what just happened. It's not that you didn't deliver. It's that you promised something, and then when delivery time rolled around, you justified yourself by saying, "Not my fault," instead of being proactive. Even if it isn’t your fault. The problem stems from the timing that was in your hand.

I take an average VP, PM, engineer, or designer who is reliable and transparent any day over the hot shot that delivers the best work but constantly needs to be reminded that a deadline is around the corner.

Reliability beats quality in this regard.

How to manage the trouble funnel

I always thought about "Managing up” like a funnel. It’s a skill to manage a funnel where you start with promises, and at the end of that funnel, there is a really bad outcome: you’re in serious trouble.

In other words, you need to reduce the chance of anything going through to the end. The best of us can’t avoid some stuff going through in the individual stages at times.

But we can manage every step individually to reduce the chance of the ultimate bad outcome to close to zero. This is an almost daily struggle for someone who is not naturally well-organized like me.

There are expectations, fail safes, and when everything fails - how you handle a crisis:

1. The # of promises you commit to: Expectations you don’t wake can’t be disappointed. The solution is not to never promise anything but to be more selective about your promises.
   Things are expected of us in any job we have; whether we have these expectations towards ourselves or from our manager, we tend to promise too much. Instead of temporarily pleasing people with a good promise, ask yourself whether it’s necessary. Nailing three promises is better than nailing five and missing one that shouldn’t have gone wrong.

2. The # of important promises: It matters obviously also whether something is important. Be wary that what looks unimportant in your backlog might carry a different importance to the person you promised it to. It may take me three hours to prepare a financial report and three hours to finish a presentation. One of those might be more important than the others. If unsure, ask.

3. The # of promises with a deadline: Not all promises come with deadlines, but those that do, are dangerous. If you promise something with a deadline, then the person you promised it to might also pass that deadline upwards. Look at it like an investment. Pulling it off will advance you even (because it advances your manager); if you don’t, you will pay the bill. The more the deadline travels upwards, the more s*** will roll downhill if it’s not happening.

4. Realistic time management, buffer: I’ve been in this industry for over two decades. I can’t recall a single period where I constantly underestimated the amount of work something takes. I’m still overestimating my capabilities. Everything takes longer, always. Whatever your method is, assume that things might take longer, especially if you haven’t started working on them. No matter how sure you are, assume that you need a hefty buffer. Always.

5. Not letting important become urgent: This one is crucial. Sometimes, we don’t think we are off track, but we already are. Something needs to be delivered tomorrow, and while you’re doing it, you get the sinking feeling, “Shit, there is more to this than I thought.” Often, we can compensate with extra work, but sometimes not, and it’s usually because two of those implode at the same time. This is only a problem when something important isn’t urgent originally. You created the problem in that case by mismanaging expectations.
   The only way to avoid this is to get important things done with priority, even if there is enough time left, and by having them in your face daily:

   1. I have a book where I use one page daily in the morning to write down what I want to do. At the beginning of the book is a page with three Post-its.
      On it are the top three things I cannot fail at. It’s also usually not a task but an entire project or client that’s important. When I led the product at Jua for instance, “Performance Evaluations,” “Board Meeting + a date,” or simply the name of an important account we were handling at the time were there.
      This list catches especially stuff that was initially far in the future but slowly crept forward.

6. Regular, open communication: Sometimes, we don’t know we’re close to messing something up despite our best efforts. Communicating openly about your priorities is an essential failsafe.
   Communicating with my peers regularly on what’s important to them and me means there’s a chance of catching something that went through all the cracks. This is especially crucial in senior leadership. If you listen to other people’s priorities, you occasionally hear something where you go, “Oh crap, I forgot, that’s right, I should also contribute to that particular thing.”
   And because you’re leading other people, your reaction time to do something about it is longer than an operator who forgot something that they can deliver by themselves.

7. Honest crisis management: It happened. Despite all the above steps, something important you promised exploded in your face even though it should not have happened, and you’re aware of it. Breathe. Sit down and think about what the best course of action is. Consider a new realistic deadline, whether something can be salvaged from the situation, and take the hit if it’s too late.
   Sometimes, nothing can be done, and you will put people in a bad position. Weaseling out, brushing it under the rug because you’re afraid can make a now bad situation worse.
   By handling a mess that you created this way, you might even score with some leaders like me after the dust settles.
   Be accountable.

I still remember the first performance evaluation that I received over twenty years ago from a badass manager I worked for. She told me that she appreciated that I was always honest with her when things went wrong. I didn’t realize back then why this was so important to her. It took almost ten years from that point for me to become a manager myself to understand why.

I was a big mess at the time, but I can say with honest reflection that I was at least always accountable when things did go wrong and got up again with a wish to do better next time.

And oh boy, many things went wrong because I was comically bad at the other steps until much later in my career.

A useful exercise is to take this trouble funnel and ask people around you how they perceive you in the individual steps. I constantly heard that I promised too much, too fast. Never too little.

Summary

Overall, there is more to “Managing up” than just how to be reliable. You also have to be clever in how to talk about your achievements and so forth, but that’s a topic for another day.

This will eat or make you in your career before anything else. If you can’t manage your promises and expectations, you will eventually get into trouble, regardless of the quality of your work otherwise.

Get it right, and you’re ahead of most of your peers.