The Environment I Need to Succeed At Work

Thomas Lewandowski
6 min readNov 22, 2022

Five things — Autonomy, good boss, bias for action, strong morals, and strong transparency — are all key to my success.

Photo by Annie Spratt on Unsplash

I’ve been reflecting a lot lately on work and what it means to me … what experiences in my past have been good or bad for me, specifically in my role as a product manager and my relationship to my boss and executives.

With reflection, I discovered five things that are most important:

  1. Autonomy
  2. Good boss
  3. Bias for action
  4. Strong moral character
  5. Strong transparency

By sharing with you today, hopefully they resonate with you and your experiences. I hope they help you determine what’s the right work environment for you, so you can find that fit and do awesome things.

For reference, these are similar to the 4 criteria from one of my earlier articles. However while those criteria are more on the tangible effects, this article focuses more on the intangible effects such as culture.

(1) Autonomy

At a basic level it means don’t micromanage my work. To be honest though, no one will admit to being a micromanager, even if they are lol.

But it’s more than just micromanagement. It’s how much your boss trusts you to do the right thing.

My best work experiences were when I had that trust from my boss. As a product manager, I make many small decisions every day. Some are risky. Not all of them work out.

When I have a firm base of support, then I am empowered to make these decisions and take risks, both big and small. I’m inspired to do the best work I can possibly do — all to create value for the user and company.

Steve Jobs said it best:

I don’t hire smart people and tell them what to do. I hire smart people and THEY tell me what to do.

(2) Good Boss

Trust from my boss is core. Beyond that, it’s a sense of encouragement and empowerment that inspires me to do my best work.

Generous with praise

I respond better to positive feedback. Some bosses were very stingy with their compliments and only said good things once a year. That wasn’t good, as I felt like I was taken for granted.

Sets me up for success

A good boss recognizes my strengths and puts me in situations where they know I will succeed. For my weaknesses, they are patient and willing to work with me to improve them.

Fights office politics for me

Every office has politics, even though they say they don’t lol. It’s just a fact of life. A good boss is a “warrior” who is willing to fight for me and my projects to get the attention, resources, and support I need.

Career growth is a must-have

Finally, career growth is not something we address once a year at performance review time — already a time of much worry and angst on both sides. Career growth is something we are constantly working on together.

A good boss makes the path for promotion clear and actionable. In the long term, they advise on what you need to do to grow into the career you really want. Bosses expect us to make short, mid, and long term plans for our company’s product. Similarly, it is just as important that we create short, mid, and long term plans for career growth too.

(3) Bias For Action

As a product manager, my role is to deliver value to our users and to the company overall. We deliver value when we launch new features. Launching is what causes us to grow users, grow transactions, grow revenue, squash defects, and just plain profit.

Execution brings results. Talking does not bring results. It’s quite basic, but many people still gloss over how important execution really is.

When we spend more time pondering about what we “could be doing” rather than writing actual PRDs and GTM plans, then that bothers me.

When we spend more time debating each other in meetings rather than investing in user research to hear it it straight from the customer’s mouth, then that bothers me.

And when we have a risk-averse environment with a lack of urgency to build and ship features, where we are unwilling to make even the smallest feature changes and improvements rather than empowering our employees to do what they sincerely believe is right for the user, then that really bothers me.

I strongly believe in the concept of MVP. I strongly believe in the concept of “moving fast and breaking things” aka “fail fast” aka quickly iterate to find a good product-market fit. I feel good when we launch things, because we’re doing what we’re supposed to be doing which is delivering value to our users. At the very least, trying something to see if it does deliver value.

Quite simply, at the core we need to move and we need to build. If we don’t, then our users will continue to suffer their pain points or an opportunity will remain fallow. Either way, it will just be a matter of time before someone else out-innovates us and beats us to that market. It’s that simple.

(4) Strong Moral Character

Overall this means people who are genuinely good and nice at their core. Not just pretend to be good and nice, which everyone does at work.

This means leaders who say all the right things in public such as at all-hands meetings. It also means implementing those principles in real life when it comes to their actions.

But to be honest, few people nowadays are as overtly bad as Travis Kalanick or Harvey Weinstein. What’s more troubling to me are the grey areas:

  • Borderline NSFW jokes at all-hands meetings
  • Cursing in a positive light such as “let’s f — ing go” but uncensored

Both make the risk of normalizing these bad behaviors (NSFW jokes and cursing) at work, a place where they definitely do not belong. Especially when they come from leaders who are supposed to lead by example.

People (both executives and individual contributors) show their character in private as well. Ideally this means there’s not much of a difference between a person’s public and private personas. A big difference in itself is a worrisome sign.

For example, character comes out when you’re at the bar together after work or sharing an Uber/train ride home together. Cursing, gossip, and similar base behavior reflects very poorly on a person.

At least as long as we’re still in the same company and have the potential to work together. If we’re ex coworkers, then we can pretty much say whatever we want to lol.

(5) Strong Transparency

Finally, I value an environment with strong transparency when it comes to both projects and culture.

First on projects, this means no siloes, no top-secret projects, no secrets we can only share to certain people. Even the traditional siloes of financials, salary, and fundraising are breaking down nowadays.

There’s certainly a difference between talking shop internally and external discussions with the media. But once you are invited into this “walled garden” you can in theory learn about whatever anyone else in the company is doing. Not only is this nice to have, but for a product manager it’s a must-have as we have to learn about intersections and dependencies for our respective engineering team as soon as possible.

Second, transparency extends to our culture and people as well. One value from Deliverr that I really enjoyed was “honest and direct.” It meant the ability to ask tough questions, especially to leaders at all-hands meetings, and then get honest and direct answers.

It wasn’t BS or misdirection like a politician. They went straight to the heart of the question, they directly addressed our worst possible fears, brought us back to reality, and then left us with optimism. That’s what good leadership does — both honest and direct.

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Thomas Lewandowski

Product Manager, Innovator, Entrepreneur. Need advice on your next project? Visit www.tl-consulting.org