Islands of Trust

From the mouth of Eric Ries

I’m going to assume most of you have read “The Lean Startup” by Eric Ries. It underpins much of how modern digital businesses try to operate, with concepts that encourage rapid failure, building the minimal valuable thing, prioritising validated learning and more.

But have you read “The Leaders Guide”, also by Eric? I found it harder to get on with than The Lean Startup, but a few concepts really resonated. In particular, one of those was “Islands of Freedom”. Eric tries to articulate ways in which we can foster an entrepreneurial culture within established businesses.

Why?

Or rather than why, perhaps the question is when?

I think empowering entrepreneurial behaviour delivers the best results when there is a complex problem space, where the solution or best path is unclear or one of many, and where even the problem is poorly defined. This yields an opportunity to differentiate through a creative approach – and that is what entrepreneurs excel at. The point is to aim for better solutions, to encourage disruption over incremental improvement.

To make this tangible, running a team tasked with a loose mission and broad responsibility is a good enough example for me to benefit from entrepreneurial thinking.

Bad examples are when the problem is well defined, the solution is reasonably well known or one of a few defined options, and there is little opportunity to differentiate for advantage.

How?

I won’t try to recreate Eric’s content, but I’d summarise my interpretation in a few key points;

1. There’s a problem, or “problem space”, so you must agree on the high-level problem statement or context.
2. There’s a lot of unknowns, variables, and unpredictability, so the entrepreneur must be trusted by the management.
3. There’s commercial (or equivalent) pressure that can be measured, so there must be accountability for results.
4. There’s an acknowledgement the challenge is hard! So there must be support, in the form of resources, tools, coaching/advice, and more.

This means relatively simple tasks must be done (informally usually for me, but I am playing around with more formal approaches) such as defining the required outputs and how they should be measured, defining “guard rails” or non-negotiables, and outlining the resources (people, money, etc) that are available to the entrepreneur.

It allows the entrepreneur to focus their creativity on defining, understanding, and solving the problems that you hired them to address, while remaining focused on using the resources they control or influence. It forces an incredibly strong mentality of ownership, craftsmanship, and in turn responsibility.

This all sounds so vague, which makes it sound hard. What do I really mean? Again, take it back to the team with the high-level mission. At its simplest, a common understanding of what problem they’re here to solve, and a known team, tools, budget and metrics, and you can get started. Islands of Freedom (or trust) operates on a sliding scale for me – the more senior the individual, the wider the responsibility they have, the more resources they have, the more I shoot for an island.

Easy, let’s get cracking!

Not so fast!

Having defined “islands of freedom”, let’s move on to the main point of this post. It should be clear that in as many situations as I think it is appropriate, I use some element of this method to manage my direct reports’ work.

So why did I call this post “Islands of Trust”, and not “Islands of Freedom”? Because freedom requires trust, and “trust” is a word often underestimated in gravity. Real trust is hard. If there is one phrase I’d like you to take away from this post it is this;

“Trust requires personal risk”

What do I mean by that? Well, coarsely put, in order to trust my directs I have to be happy that at times they are doing what I think is the wrong thing. If they’re doing everything how I would have done it, I am not trusting them, I am not empowering them to innovate, I am forcing them to think like I think, and reducing the collective brain power and velocity of my team. It is critical to minimise rules if you’re to maximise creativity. I want to allow them to use the flair that I hired them for.

I must carefully listen to them describe something they’re doing, feel critical of it, and bless them continuing down that path, even though I am unconvinced that they’re doing the right thing.

And in doing so, there is a risk that they will fail, and ultimately, I am accountable for that. Therefore, in order to see my team excel, do the best it possibly can, learn how to be better every day, and move as quickly as it is capable, I must be committed to the inevitability that I will be explaining, defending, and recovering from or compensating for their failure in the future.

Risky, huh? But risk is calculated and measured if you’re doing it well. Besides hiring awesome people (an essential ingredient), how do you know you’re on the right side of “calculated trust”?

The key to convincing me that the risk level is appropriate is that they must be able to explain their approach in a way that demonstrates grasp of the problem, understanding of the people, technical and any other relevant context, and, critically, for them to have an idea around the tolerances – that is, I want them to set their own boundaries that say something like “if XYZ doesn’t work”, or “if we get to XYZ date”, or “if XYZ person doesn’t like that”, or “if XYZ research proves that wrong”, and a corresponding action. I also expect them to actively seek my opinion. Fundamentally, I’m expecting them to show the qualities I look for in my Leadership Philosophy – willingness to be on the wrong path (“Be wrong”) and change approach if they are, and to listen to what is around them, including the context and their manager, me (“Be listening”).

Got it, so you add no value then, Simon?

Wrong. You see what I need is for my directs to trust me too – I need them to proactively seek my opinion out, to discuss problems they have with me openly, to allow me to coach them and guide them, to educate me about their strategy so that I can represent it, and to know that I’ve got their back. I’m very confident in the value I bring when I am doing those things. I’d see an inability to trust my directs as a potential indicator that I was lacking confidence myself; if I have to have all the answers, what am I intimidated by?

The worst manager-to-direct relationships I’ve had have been when trust in either direction breaks down. The best ones have been when trust is implicit. That trust needs maintaining, which takes effort from both, but the best way to secure that trust initially is often for me to make the first move, and offer my trust first.

Some secrets

I’m not stupid (or rather, have not yet been irrefutably proven to be), and I know this can go wrong. So there are caveats;

• Not everyone has got the entrepreneur in them. Some people need leading to that way of working, some will never thrive in that environment. Knowing who should be treated like this is a skill – and I’ve gotten it wrong a fair few times.
• Choosing to trust someone is not always enough. I observe how they work, watch from afar (hint: I lurk on slack occasionally, shhh!), and build my understanding and confidence based on evidence. The better I know how they work, the more I understand them, and the more trust we have, the more freedom they get. Perceived trust, by them or by their team or peers, is sometimes as important as trust itself.
• There obviously must be boundaries. Some of those are the “guard rails” I described above, but there are also times when I just can’t support a particular approach. A healthy, trusting relationship makes them more receptive to those infrequent “err, hold fire, I think this is a bad idea” moments. Once they're used to freedom, it can be difficult for an entrepreneur to take a clear directive steer, though, so this is important to get right. It's caught me out before, and will again.
• The value that a leader following this pattern brings is harder to observe from a distance. That means stakeholders need to be comfortable that I am appropriately engaged in what any of my 'entrepreneurs' are doing. I get this wrong all the time, both my level of engagement and how that is perceived; it's a constant balancing act and stakeholder management challenge, especially when I'm stretched. This increases the personal risk, so in some ways has a feedback loop into how I evaluate my comfort with “calculated trust”.

That’s it. So ask yourself – are you ready to take personal risk in order to get the most from your team?