How do I deal with ambitious goals and ambitious bosses without losing my sanity and my team’s trust? If you’re in middle management, this is probably something you ask yourself quite a lot. Not a difficult question? Let’s give it a dash of self-doubt. Was the task really impossible or was it I who lack ambition and a can-do attitude? 

One thing I have observed dealing with individual contributors (IC) transitioning to management, is that they tend to try to solve every challenge at their level. And it’s often because as an IC, you have tasks that need minimal coordination with other people. It’s quite rare that you chase your manager for something; it’s the other way around. You have full ownership of tasks. The impediments you encounter relate to technical skills you haven’t developed yet. This mindset is fine but applying it in a management role is tricky.

Solving challenges at one’s level is not in itself bad. In fact, every manager would appreciate having junior managers who need little assistance. But not knowing when or how to manage up can be a big concern. This is often the reason why a business strategy dies at the middle management level. If you’re a middle manager struggling to manage up, this is a familiar scenario. Top management wonders why it takes a long time to get results, ICs reporting to you think that they always have to sacrifice, and you feel that all the weight is on your shoulders and you want to quit.

So how do you address this? There’s a good chance that you’ve started reading books, watching videos, and even attending training sessions. After all, this is how you addressed your skill gaps as an IC. These things work for some of us but some still struggle and ask the following questions when presented with a new challenge. If I say no, won’t my manager think that I am incompetent? If I say yes, how can I push my team to work on another ambitious goal? The fact that you have these questions means you are not equipped to make the decision. And what could be stopping you from raising concerns is a possible reputational impact from the first question. But should there be any?

As I have observed, this is often the middle manager looking at a management challenge with the eyes of an IC. You think that saying no and raising concerns is admitting a skill gap. But as a manager, you are actually expected to be transparent about challenges. And these challenges, unlike your IC tasks, need coordination of multiple people–it is not all on you.

But still, how can you navigate through this tricky discussion about ambitious goals? One trick I can offer is in the title. It seems dumb but there’s actually more to it. When presented with a difficult challenge, some of us have the tendency to say no, because of this or that. No, you can’t accommodate another project because you’re understaffed. No, because the other business unit requires 2 weeks of lead time. No, because we only have 3 days before the holidays. These can all be valid reasons but this response format has some disadvantages. For one, these are not the responses you yourself would love to hear. Also, this type of response prevents you from exploring possibilities. And if you think about it, doesn’t it look like you are deciding for both your boss and your team in one response? Still wondering now why you feel so much pressure?

The yes-but format offers a shift in mindset. Yes, we can pick up the project but with only 4 people, we have to push back a couple of in-flight projects. Yes, we can do it but we need to find a way for the other business unit to respond faster. Yes, we can beat 3 days but we have to trim down the specs. As you can see, this triggers creativity, presents the risks better. And above all, this allows your boss to decide with you. Doesn’t that lighten the load a bit?

Of course this trick and managing up is not the key to everything that’s good in your professional life. We’d still meet unreasonable bosses and organisations that could need a major overhaul in their processes. But there will always be something you can control and you can start there. -mB


Cover photo by Luis Villasmil on Unsplash

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