Surviving a Chaotic Boss

When you are trying to be organized and strategic, and it’s your boss who is chaotic, reactive, and causing confusion and rework, it can make you feel really stressed, confused, frustrated, and tired!

It’s a shame there are so many chaotic bosses out there, but they are indeed out there, so we need to find a way to make the best of it.

Ruthless Priorities…

This question came up in a discussion in My Executive Mentoring Group about focusing on Ruthless Priorities, and the idea that you can’t do everything so you need to negotiate with your management and stakeholders to give yourself the opportunity to focus on and finish the most important Ruthless Priorities first.

(More on Ruthless Priorities here)

The Chaotic Boss…

But here’s the question I got:

What if you try to get an agreement with your management on the ruthless priorities and focus on them, but management insists on you having to do “everything”, and the quality/scope expectations don’t budge, either?

I had several conversations with my manager where I explained that I don’t have time for everything they want me to do and we need to schedule deliverables, but it’s a startup and they want everything right away. They don’t seem to care that I deliver something every day, they keep saying what I have not delivered. I can’t focus on the big and strategic, there is always urgent firefighting to do.

Any ideas on how to deal with the communication aspect?

I see a few key ideas in this question

#1: Recommend Priorities

The question says, “They get upset when I ask them to help me prioritize my workload”.

To put Ruthless Priorities into action…

…you need to do the work up front to prioritize your workload and present recommendations to your manager.

If you ask them for help with setting Priorities, you are giving your manager that work to do. You need to do it.

You will distinguish yourself if you come in with a recommendation and say, “I will finish these 3 things first because (insert why it’s so important to the business), I will work on the next 5 in the background, then after I finish the first 3, I will take on this one big project. I actually recommend we delay these other 5 things because we will get a better outcome if we have the information from finishing this project first…”

I can tell you that as an executive the high performers were the ones who drove those kind of conversations and negotiations with me, not the ones who said, “This is too much work, and I need you to sort it out”, or “This is too much work so I need more resources”.

Dealing with an impossible workload and finding a doable path forward to get the right things done is at the heart of Ruthless Priorities and is a big part of leadership (and why leadership is hard.)

#2: A Startup

All that being said, the rules in a start-up can go out the window. There is often an implied (or stated outright) part of the culture that is: We are all going to work ourselves to death because the opportunity is so big and the timeline is so short.

If you try to inject some prioritization or even a little process, the culture can reject you by saying, “That will ruin everything. And we don’t have time for that. We just have to GO”.

In reality, most startups do not succeed, (about 2 of 10 do) and in my opinion, this is one of the reasons. Sure sometimes brut force and sheer will will get a startup over the line, but it is the exception.

The crazy, unmanaged chaos is not the magic differentiator, nor a repeatable formula for success.

I have seen some start-ups function well in a fast-paced, aggressive, but organized manner, and they do not lose the magic. Chaos does not scale. But this is a topic for another article…

My advice to people in this situation is if you are in a start-up, make sure it’s because you are in love with the mission, and you are personally motivated to work in whatever way is expected to make it come true. Otherwise a startup is just torture.

Never go to a startup just for the money. If you are at a startup just because you need the work, or you are in it for a huge payoff, but you do not personally care about the mission, you will be miserable, because you will be expected to sacrifice a lot of your life, energy, and well being to be a part of it.

It can be worth it, just make sure that it is worth it for you, even if you don’t get the big payout.

If the executive management in a startup is chaotic, you are not going to be able to change it from below. But you can still try to recommend some structure and priorities for your own work, which gets me to the last part of the question…

#3: Communication

In the Ruthless Priorities Class, I talk about the idea of a Catch List. I won’t go into the details here, but the idea is to keep a list of everything that is asked of you and use it to both set priorities and communicate about your workload and work plan.

If you can show your boss with your Catch List that “everything” = 200 things requested over the past 2 months, and they are asking for 10 more randomly this week, put the next 10 on the list of 200 and show them the whole list every time.

This creates helpful context.

Then when you recommend priorities, you can demonstrate that you are actually getting the most important stuff done, which is hard to argue with. If they say, “That’s not good enough, we need everything”, you can show them the Catch List and say, “It’s all here. I haven’t dropped anything”.

It’s harder for them to insist on your getting 200 things done this week if they are looking at the list with you.

By using a Catch List to negotiate priorities, you can build your credibility and create a more do-able work load.

Patty Azzarello

Patty is available to speak at your company, annual meeting, or customer event. She can also deliver a custom workshop on Leadership or Strategy Execution for your leadership team. Contact Patty.

Or if you would like some personal help on your own professional development, check out her Executive Mentoring Group. It’s filled with insights, resources and support to build your executive confidence, advance your career, and includes direct mentoring from Patty.


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Patty Azzarello is an executive, best-selling author, speaker and CEO/Business Advisor. She became the youngest general manager at HP at the age of 33, ran a billion dollar software business at 35 and became a CEO for the first time at 38 (all without turning into a self-centered, miserable jerk)

You can find Patty at, follow her on twitter or Facebook, or read her books RISE and MOVE.

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