In the realm of modern leadership practices and principles it has become very en vogue to claim that one’s role as a leader is to “hire great people and get out of the way.” Certainly hiring great people and not actively creating barriers for them are easy to agree with — however, there is in fact more to proper stewardship of creative professionals in their evolving careers. Much more.

Some years ago I did a very in-depth 360 review, and the biggest takeaway for me as a growing leader was that the aspects of my leadership that are hard for people are also the same things that people like in my style. Almost every hole in my leadership game was clearly the opposite side of the coin from a strength.

For example, the number one thing people stated they appreciated about working with me was that I truly trusted them and gave them space to work, try things, even to fail; the promise of autonomy was something that I was able to consistently deliver on. Now the flip side of this strength is that there was a perception, a consistent sense that I had advice, some specific direction that I had up my sleeve. People often felt that there were ideas, approaches, and directives that I kept to myself. In the most negative circumstances, people could be left to feel that I knew what I wanted them to do but wouldn’t say it directly. No bueno.

Of course, what I was trying to avoid, often to terrific effect, was overly directing people so that they lost ownership of their work. “Give people problems, not solutions” was a mantra I related to and believed in, and wanted my own supervisors to follow.

It turns out that sometimes you do have to give more than just the problem. As leaders, we owe it to our people to be transparent about our information, thoughts, options, and (importantly) biases with regard to a certain problem.

How do we square this circle? We want to give people true autonomy whereby they are making good decisions without having to consult us first and feeling invested in and ownership of the result and associated learnings. But we also have empathy for our people and know that they are following us for a reason, and a big part of that reason is that they seek our counsel and to see the world through our eyes, or at least be able to.

Let’s also face the reality that if we provide autonomy and our people fail to explore a path that we thought was a smart one, it becomes hard not to judge their performance negatively, and perhaps unfairly so.

We want “do it your way” but we also want “do it as well as I would do it.”

Here we see the answer: Provide a starting point, a “sane default” for a given problem, and clarify that if the individual (or team) finds fault with the approach they are free to choose another approach.

“Do this, or something better” arrives as our new leadership mantra.

Let’s give our folks a suggestion of what to do, and also the context and support to change course as, in the immortal words of The Dude, “new sh*t has come to light.”

After all… “fail to plan, plan to fail” and ALSO “no plan survives first contact with the [problem].” Both, of course, are very true.

In terms of a lens for viewing our direction, I find it helpful to look at these four aspects, providing a starting point for each and encouraging evolution beyond my own thinking on ALL of them:

  • Factual nature of the problem.
  • Assumptions and past learnings.
  • Options for proceeding.
  • Measurement of success.

If nothing else, we owe our people a good start on the factual nature of the problem and a clear measurement of success. However, no matter how firm these starting points are, our people need to be able to pressure-test them.

On the matter of facts, more facts are always welcome, and our people ought to be keenly in search of and on the lookout for additional first principles information. When it comes to measuring success, the principal pressure test here is often “if we move this number, will it really matter?” Our responsibility here is not simply to remind people that they can test us as leaders, it is in fact that they must always satisfy for themselves that the goal is worthwhile and impactful.

Assumptions, hypotheses, biases, past experience, and perceived learnings are perhaps the most fungible aspects of the context here, and the most likely to evolve based on what our people learn as they work through the problem. We ought to name our biases (survivor bias, or “what’s worked for me was…” is particularly common) and inventory our perspective plainly and unemotionally. “This is my take. It is what it is, take what’s valuable and leave the rest” we say.

With regard to the options available to us, the most common pattern here is to expect, encourage, and embrace the expansion of options. “Write out all your options here, even the bad ones,” we say. As leaders, we will often know of at least one possible option, and we almost certainly do not know all the possible paths of actions. This is a natural motion on both sides and intuitively reinforced by our mantra of “do this, or something better” as it speaks to the very heart of developing alternatives.

I continue to try to square this circle and offer my team true autonomy without leaving them twisting in the wind looking for a starting point.

As you try this in your own evolving leadership style, be prepared for the stark reality that sometimes your initial idea was the best idea anyone could find… and that the opposite may more often be the case.

Love and light,



  • Christopher O'Donnell

    Chief Product Officer

    Thrive Global

    Christopher O'Donnell is Chief Product Officer, overseeing Thrive's product and engineering team. Christopher spent over ten years at HubSpot, most recently serving as Chief Product Officer overseeing all product and design for the global team. Under his leadership, HubSpot was ranked second in product satisfaction by G2’s Best Global Sellers for 2021, behind only Microsoft. In 2019, he was named one of Comparably’s Best Product Leaders. An established public speaker and guest lecturer at MIT Sloan, he has given product keynotes at INBOUND for years, with audiences of 10k+, and he is also the leader of the band The Providers, with 10M views on YouTube. Prior to his time at HubSpot, Christopher co-founded, a javascript error tracking application that was ultimately acquired by Twitter and then Google. Before that, he was Director of Product Development at Performable, where he led the design and development of Performable Analytics and Engage before the product and team were acquired by HubSpot in 2011.