Listen Up: How Do You Really Know What's Going On In Your Company?

Margaret Heffernan's accomplishments are far too many to list here, but they include veteran CEO and entrepreneur, author of five books, including "Wilful Blindness," a finalist for the FT Best Business Book award, and TED speaker whose talks have been viewed more than nine million times. I'm also proud to call her a colleague at Merryck & Co., a senior leadership development and executive mentoring firm. In my interview with Heffernan, she described some of the most important insights she's shared with leaders about understanding what's really happening in the culture of their companies.

Q. What are the most common themes that come up in conversations with the senior executives you advise?

A. One theme that comes up, partly because it’s on everybody’s mind and also because my clients tend to know what I’ve written about, is about “how do I know what I need to know?” In other words, how can you be confident that you’re not willfully blind, to which the obvious answer is you can’t ever be certain. You never will be. But what can you do to at least reduce the risk that you’re missing something really important?

That then raises questions about where your information is coming from -- how do you know that it’s trustworthy, what questions are you asking, and how much do you trust the hierarchy that edits what you hear and what you see? And how far are you prepared to go to break the hierarchy in order to reassure yourself that you are seeing and hearing the stuff that really matters? That then leads into discussions about how the hierarchy is working for you and how it is working against you.

And what are your working assumptions for how you’re approaching your job? A lot of leaders haven’t really necessarily adapted their thinking to changed circumstances, so they’re operating with many of the assumptions that got them to the top, many of which may not be true anymore or may not be true in that job.

Q. What are some of the challenges you see them facing when they finally get the top job?

A. As you climb the corporate hierarchy, you’re constantly constrained by what you can and can’t do. You have your job description, your goals and targets, and your boss’s goals and targets. And when you get to the top, you have quite a lot of freedom, but you haven’t ever had that. Many people who find themselves in leadership positions can feel a bit like the cage door is open but nobody’s confident to go through it.

"Many people who find themselves in leadership positions can feel a bit like the cage door is open but nobody’s confident to go through it."

The reason is that the constraints in their minds are so profound and ingrained. They have had such long careers of looking for approval that the idea that they have the opportunity to think freely for themselves takes quite a lot of getting used to. That transition can take some work.

Q. You mentioned the blind spots earlier. What are the best tactics to uncover them?

A. It helps to have people in your organization who have worked with you for a long time. In three of my technology companies in Boston, I had a couple of employees in each one who had worked alongside me for a long period of time and knew me very well and were smart enough not to be afraid of me and really would tell me the truth. And I would have been blindsided without them. So those long-term relationships are very useful, so that people will tell you the truth and also so they can model the quality of conflict you want to foster within the organization. You have to create an environment where it’s safe to have arguments.

The other thing that is really useful is the age-old technique of skip-level meetings and brown-bag lunches. You have to be really patient because in the first three or four meetings, either nobody will turn up or nobody will tell you the truth. But eventually somebody will get sick of the platitudes and burst out with something that everybody else is thinking and then you’re started.

Another good approach is to say, “This is a decision that we’ve all reached. We’re all going to sleep on it for 48 hours, and then we’re going to come back and share all the second thoughts we’ve had since then.” Most people do a lot of really good thinking away from the meeting, and you want to capture that.

It’s also helpful to articulate decisions as hypotheses. A decision is basically a way of saying, “We believe that if we do X, the following will result.” And there’s a really great second question, which is, “If we’re right, what would we expect to see, and if we’re wrong, what would we expect to see?” That creates a much lower barrier of resistance to having a good conversation about the decision before it's final.

Q. What are the insights you’ve gained about functional and dysfunctional corporate cultures? What are the biggest momentum killers?

A. In this day and age, it’s hierarchy, bureaucracy and diversity. If the hierarchy’s too rigid, if the bureaucracy is too profuse and if there’s very little diversity, you’re going to be in deep trouble, no matter what business you’re in.

The hierarchy is going to enforce obedience and conformity and it will leech responsibility out of the culture because people will say that everything is the responsibility of the person above them. 

Bureaucracy means people do exactly what they’re told. So if the house is on fire, nobody’s going to put it out because that’s not in their job description. And if they can’t hit their targets the right way, they’ll hit them the wrong way. If you put those two together, nobody’s going to say when a strategy’s stupid or bad or unethical or illegal. 

And without diversity, you’re not going to have enough debate to have any meaningful innovation. If you put those three together, you’re in big trouble.

Q. What do you see as the X factors that separate a great executive from a really good executive?

A. Context is everything, but my candidates would be curiosity, generosity and skepticism. If they don’t keep learning all the time, they’re going to be in trouble. And if they don’t make people feel valued, they’re going to be hung out to dry. If they don’t have a habit of mind that’s constantly saying, “I could be completely wrong here,” they’re going to be in trouble.

"No matter how tumultuous the operating environment, they always have energy. They experience everything, including failure, as an opportunity to learn more."

I’ve had a number of clients who are such gracious learners. No matter how tumultuous the operating environment, they always have energy. They experience everything, including failure, as an opportunity to learn more. So they are constantly adapting as their environment shifts. They can be very challenging to work with because you have to keep up, but they’re just phenomenally good fun.

Q. What has been an important leadership lesson for you personally?

A. Many people look at my career, going from radio to television to high tech to writing, and they think, this is really strange. And it may be unusual, but everything I’ve done has really been about working with extremely creative people, trying to do something that’s never been done before. That does require a very particular kind of leadership, and I love working with people who other people regard as difficult.

Q. Can you parse that skill for me of working with difficult people?

A. I’ve always been more interested in what people want to do than how I can manipulate them to get them to do what I want. If you have a lot of creative people in the room and you really understand what excites them, you can always do incredible things. But you have to get into their heads and see what’s there and respect it and put it in a place where everybody can see it.

And I’ve always worked in industries that are about risky products, with a very high degree of experimentation, that required enormous comfort with uncertainty and ambiguity. It just turned out that that was the way the world was going anyway.

Q. What is your favorite job interview question?

A. “Who helped you?” The reason I always ask that question is because people who are generous and helpful themselves always remember the people who helped them. And the people who can’t are the people who take all the credit for their own success and don’t inspire generosity in other people.

If you have an organization full of helpful people, information flows much faster to solve problems very quickly. I often think that the acid test of an organization is how fast does information flow to where it has value? In very competitive or very siloed organizations, it gets stuck and it gets stuck quickly. But in really open, helpful cultures, it moves very freely.