TBM 345: Back On Track

Apologies. For family reasons, there was a longer-than-normal gap between posts (10 days). We're back on track now, so watch for new posts. I'll start with a quick one (a three-in-one) to get back into the groove.

Three short thoughts on change and leadership.

Transforming vs. Showing

Transformation (and change in general) is difficult, no matter how skilled your team is. I would argue that is a distinct skill from product and more general leadership.

I love Atlassian's Tanguy Crusson's honest take here:

Honestly, I'm not sure a product leader would have the patience to see it through once they understand how long it takes to turn an org around. IMO, it's two different jobs: the product leader can help the rest of the org witness what that work model looks like (e.g., pilot setting, you need to see it to understand it's possible in your org), and the expert in org change can then drive the rollout. By the time it's done, I would guess many product leaders would have come and gone. It takes a village 🙂

Tanguy's take matches my experience. Some leaders are much better at showing what great looks like than navigating a protracted period of "influence not authority." Meanwhile, leaders who specialize in change and transformation often have the reverse problem. During periods of rapid disruption, they may be too risk-averse and unwilling to ruffle some feathers.

An acquaintance learned this the hard way recently when they were unceremoniously fired after struggling to adapt to the company's "vibe shift." This person had led an objectively effective change effort for three years—an effort frequently applauded by the C-suite, board, and even customers.

But rapid shifts in their business changed that.

In retrospect, it was like someone had flipped a switch, and I had missed it. We weren't in that transformation mode anymore. I had a lot of trouble matching people's shifting expectations to get into everyone's business and hound people. Things I would have stepped back from a year ago to let them work out gradually in a couple of weeks—now it was like I needed to do something by the end of the day. It took me too long to adapt, and I had too much emotionally invested in the journey we were on.

Another friend with a long track record at various marquee product companies learned the opposite lesson. They were recruited to lead a group at a large company eager to shift to the "product operating model."

It was as if my whole playbook didn't work," they shared.

At the beginning, things were going great. We made fast progress. People were always asking me for my take and perspective. But I was quickly in over my head. I realize now, a couple of months after leaving, that I completely misread the gap as a skill and expertise gap. I persuaded myself that all I needed to do was be an expert player-coach. Meanwhile, there were a lot of experts at [company]. I was missing many of the skills I needed.

Final (funny) quote:

The new leader here treats us like no one has ever worked at a tech company. It is always "Well at [FAANG] we did this.' I let this go on for about three months before I mentioned that I had worked at the same company they had worked at.

Sadly, I see this often. There's a bias toward believing that existing people in the company must lack the needed skills.

The lesson here is that transformation is not simply a "has done it before" issue. It requires its own set unique skills. Think about taking Tanguy’s advice.

Context and an Expiration Date

Some basic behavior changes of leaders can leave people far more willing to try new things. Often, leaders underestimate the extent to which people are open to experimentation when there's a clear commitment to reassess at a later point.

There's a huge difference between:

"For the next couple of months, I'd love to try _______, and on ___, we will reflect on how things are going and decide whether to pivot, continue, or stop this."

and

"Going forward, the new policy is __________."

Leaders also underestimate how willing people are to tolerate something slightly annoying—so long as the leader describes a compelling future vision of what things could become. For example:

"The goal here is to limit dependencies by investing in our platform strategy. In the meantime, however, we need to implement some scaffolding to reduce cognitive load and make better decisions."

vs.

"The new policy is to hold heavyweight dependency resolution meetings."

We often talk about change being hard. As many have noted over the years, the issue is less about change and more about people hating being changed. They dislike having no agency in the situation and not being part of shaping the solution. They hate being experimented on. They hate change for change's sake and surface-level "moving the deck chairs.

So try giving some context and an expiration date. It can make a world of difference.

A Prompt to Help With Sharing Strategic Context

Here's something any leader can do tomorrow to improve the quality and speed of execution of any team or organization. Step by step:

Step 1️⃣

Send an email to everyone involved with a simple prompt:

"I am curious about your decisions that might benefit from more strategic context. To keep it simple, fill in this prompt:

I frequently find myself making decisions regarding ____________. If I knew that we _____________, I would likely opt to _____________. But if I knew that we __________, instead I would _______________.

There are no wrong answers. We'll do our best as a leadership team to provide that context. You can reply to me directly."

Step 2️⃣

Review the responses.

You will notice that many of the responses are vague and not necessarily actionable. Some people are less experienced (they are talking about decisions that are "forever" perceived trade-offs like quality and speed).

Some people are worried about being too specific for fear of getting someone in trouble. Don't hold that against anyone. Thank everyone, regardless.

But some people will give you incredible nuggets of information.

For example:

I frequently find myself deciding whether to optimize our sales and onboarding process for high-ACV deals or rapid local market saturation.

If I knew that we were committed to tipping local markets as the primary growth lever, even at the cost of smaller initial deal sizes, I would likely opt to streamline onboarding, strip down friction-heavy enterprise features, and prioritize network effects over immediate revenue maximization. This would mean optimizing for virality, ease of entry, and reducing barriers like long procurement cycles.

But if I knew that we needed to maximize ACV per deal to justify our current cost structure and sales model, I would instead lean into high-touch sales, custom enterprise integrations, and more complex contract structures, even if it means slower initial adoption and higher churn risk.

Step 3️⃣

Provide that context.

Yes, you can ask for general questions in all-hands or pop in an "any questions?" at the tail end of a meeting. But people often feel ill-prepared to answer these questions on the spot.

And you, as a leader, often feel ill-prepared to answer the hard ones on the spot.

This approach captures the context needed and the implications.