Managing Up

Managing Up

Always failing but never a failure

You will always be failing someone. In a management or leadership position, you navigate a complex set of tradeoffs and someone will always be on the down end of those trade offs.

Trying to frustrate the absolute minimum number of people takes a costly communication toll (‘ruinous empathy’) and offers a middle of the road solution that will leave everyone frustrated.

Managing is about managing failure. You can succeed through failure by anticipating failures and planning accordingly. Directly ask people how you can avoid failing or frustrating them - and clearly state if you can or cannot satisfy their concerns.

I often start with something like ‘Hey I know that doing x is important, but I can’t do that right now and also meet y business goal. How can we solve this?”. Sometimes we can’t arrive at a solution but they now know not to depend on me to deliver something I can’t deliver. We talked about it and l don’t lose sleep over it.

The failures that matter are ones where you broke a promise. Success isn’t trying to win every battle but setting expectations early about which battles you expect to win and telling people.

Take all the time you can and always ask for more time

When in a new role, everything feels new. Psychologically, problems that are “new” (to you!) appear to be very urgent and important even if empirically, they are neither.

It is paradoxically hardest to ask for help effectively when you need help the most — largely due to overemphasizing your personal experience instead of what the other person will receive.

Canned phrases can really help dig you out of the hole. A good canned phrase should do 3 things:

  1. Ask the person what exactly then need by what time
  2. Project confidence that you have everything under control
  3. Convey that delaying the project is in THEIR best interest.

For example: Our project is going great, but some new opportunities have come up that I would love to explore while we are focused on this issue - can me/my team have until [exact date] exploring this or do you absolutely need [clear statement of scope] by [date originally promised]?

Critically, you should also be very clear when you do not know. For example: I don’t know when this project will complete / have an answer for that question. When do you need to know that? [ok thanks] I will follow up via an email. By [time agreed upon].

Deeply Collaborate with people/HR team members

Modern HR is…very different from 5-10 years ago in tech. It is reasonable to assume that letting someone go for performance reasons or changing reporting structure will take a far greater amount of time than it did in the past (upwards of 40 hours of your time).

Though those hard conversations or changes are often the right thing to do for both you and the individual - they are costs that can be easily misestimated. These are very large time costs that are not clearly stated at the outset - there is no ‘expect completing this form to take x hours’ at the top of the doc. Mis-estimating a task by 5 hours can really mess up your plans for the week!

If you are struggling with team members, bring in the people team and help them understand the current needs. For example, “I need to do x, y and z for the business. I won't be able to fill out 3 pages of documentation for each of 8 direct reports before we kick off this project. How can we work together to do right by the team members and the company?” The answers are often surprising! And in my experience, much better when you bring them in than when you keep them away.

[wip] Slow is smooth; smooth is fast…in the military

Probably the central struggle for me when managing up is a disagreement about how to handle forward planning. Specifically, given the option, should we improve the speed at which we can adapt to change or plan the next year based on what we know today. My experience has been that I do not know very much about what will be true a year from now, and that planning that far in advance, with maybe a year or two of prior data to work from, is a fools errand. So, I tend to focus on reducing the friction to change both organizationally and within my team. However, those efforts get a fair amount of pushback.

The tension between moving quickly and planning

Ground conversations in the company values ESPECIALLY with vendors and partners

[security example]

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