Neil Perkin tackles some important leadership points in High-reaching informality (emphasis mine):

Overly formal environments are more likely to be low in psychological safety, and less likely to encourage people to speak up, contribute their ideas, and challenge assumptions or norms. Informality helps to break down barriers, reduces the toxicity and influence of internal politics, helps a team to get the best ideas and to be adaptive in delivery to arrive at better outcomes. […]

It’s useful to think of psychological safety as the bringing together of mutual trust and respect, and also comfort with dissent. Overly or inappropriately formal environments reduce trust down to a transactional relationship: I asked you to do this, so did you do it? Whilst dependability is important, trust is also built on competence, confidence, integrity, and empathy.

This relates to something that’s been on my mind quite a bit over the past few weeks: the question of what it means to be “boss”. The “transactional relationship” that Neil describes above is one I will always avoid with all my heart with my teams.

I was lucky early in my career. When I first joined eBay I had a fantastic manager. He was empathetic and people-first, and yet strongly business-driven. He coached me, corrected me, taught me how to speak the language of business, challenged me… but above all, it felt like he was on my side. I had someone in my corner, someone rooting for me, someone to help me navigate a gigantic organization while I really felt like I had no idea what I was doing. He didn’t react negatively to bad news or frustrated questions, he simply said, “tell me more about that.” I will be forever grateful to Christian for the way he set me up for long-term career success.

20 years later I know just how lucky I was. From my conversations with teams and candidates over the past year or so it has become clear to me that very few people have the privilege of working with a good manager early in their career—someone who is supportive yet determined for us to do the best work of our lives, together. This seems particularly acute in the middle management layer¹, where organizations spend very little time on training new leaders. From The Strengths, Weaknesses and Blind Spots of Managers:

Worldwide, the cost of poor management and lost productivity from not engaged or actively disengaged employees is $8.8 trillion, or 9% of global GDP. Changing how people are managed is perhaps the easiest way to boost productivity within organizations.

Yet, the majority of managers receive little feedback on how effectively they manage their team. Less than half of U.S. employees (42%) report having the opportunity to formally provide feedback to their manager, and fewer than one in four (24%) have formally rated their manager’s performance.

I’m not sure what the solution is, but I do think this is an important problem to call out and watch out for. Do you have transactional leaders in your company, or relational ones? The transactional leaders might initially appear to be more effective, but everything I’ve learned up to this point in my career has shown me that those benefits are short-lived, and almost always end up with disengaged, resentful team members. As leaders we are not here to tell people what to do. We are here to provide strategic direction and context, and coach our people—as part of the same team—on how to make the business and themselves successful for the long haul.

PS. If you’re looking for a book that covers these topics really well, give Good Authority: How to Become the Leader Your Team Is Waiting for by Jonathan Raymond a go.

1. See Director means something for a devastating take on this ↩︎

Two recent articles about engineering management stuck with me because they complement each other well to articulate a leadership philosophy I’ve held for a long time, but haven’t been able to put into words effectively.

First, in The Disappointment Frontier James Stanier expands on a controversial quote: “leadership is disappointing people at a rate they can absorb.” He talks about how keeping teams in a “bubble of protection” (where you act as the “umbrella” for bad news) never ends well. And even though managing disappointment is a core leadership skill, it is typically overlooked when training new managers. It’s worth reading the whole article, but here is a key point:

Managing a team of any size—from a handful of people to a whole company—is a continual balance between trying to empower people to achieve what they want (interesting projects, plentiful opportunities, a plethora of pay increases and promotions) whilst navigating a conflicting reality that doesn’t always want to give it to them. As such, there is a lot of truth to the quote at the beginning of the article. Leadership is about disappointing people at a rate they can absorb. In fact, I think that I’ve likely spent far more time on mitigation of disappointment or on managing expectations than I have on being motivational in my management career.

James goes on to give some really good advice on how to manage disappointment well. The second article is Will Larson’s Unexpected Anti-Patterns for Engineering Leaders, in which he also discusses the dangers of the “umbrella” approach:

The more senior the teams I’ve worked with, the more I’ve come to believe that protecting your team from reality just makes things worse for them in the long term. Larson now tries to throw his team into the gory details much more quickly. “In the past, I used to think I was energizing my team by sparing them the details. But now it feels like lying to them,” he says. On a tactical level, Larson adjusted this habit by buffering less information. “That means even if it’s disappointing for folks, I’d rather them process news bit by bit, rather than deal with a huge ocean of mess all in one moment.”

Obviously you are not going to tell your team every little thing that happens in your day and your meetings. But the idea that we should shield our teams from the realities of an organization is fundamentally flawed and ultimately does a huge disservice to people. If we hide the context of our decisions or guidance we lose the trust of our team—and once that happens, all is lost. This approach also stunts growth. If we don’t prepare people for how organizations work, their eventual exposure to reality will be a huge shock and we would’ve lost out on the opportunity to coach them slowly over time.

I once received some performance review feedback that I am “too transparent” with my teams, and I need to dial that down a bit. I respectfully declined. I don’t know of any other way to be—both as a human and as a manager. I also firmly believe I would be a worse people manager if I adopted that feedback.

That said, transparency is a skill. One I’ve cultivated for many years, and will likely never fully master. How and when you say things matter, and it takes time to learn those nuances. The above articles give some great advice on how to start that journey with your teams. So I encourage you to give transparency a try. I think you’ll find that you immediately become partners with your team members, as opposed to just their “boss.” And you will make magic together once that happens.