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July 2023

The Pleaser

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There’s a certain failure pattern than I have observed quite often with middle managers and occasionally with executives, and that is “the people pleaser.” If you’re exhausted from trying to build consensus up, down and across the organization, this might be making your job harder than it should be.

Being a people pleaser is a personality trait that is not uncommon. Everyone wants to please someone, whether your spouse, your parents, your boss or your board. That’s an admirable trait. But in business, if you try to please everyone, it can undermine your effectiveness. Worse, if your goal is to be liked, you may find yourself making the wrongs decisions for the wrong reasons, putting personal feelings ahead of what is best for the business.

The problem with trying to be a people pleaser comes when you deal with complex problems that don’t lend themselves to a negotiated compromise. Or said differently, sometimes you just have to make a decision, consequences be damned. If you’re trying to make sure everyone is ok with a decision, or worse, that everyone likes you, you’re going to have an especially hard time making strategic decisions.

Good decision making requires getting input from many sources. But sometimes it’s impossible to reconcile all of the input and find a happy medium. In fact, trying to find such a compromise can often result in a worse decision.

Startups often have more ambition than resources. And so when choosing between different strategic options (expand in Europe or Asia? Invest in Enterprise security or SMB ease of use? Build a reseller program or hire more sales reps?) you need to concentrate your resources and not get spread too thin.

In these situations and many others, executives need to be decisive. It’s good to get input from different perspectives internally and from your board. But ultimately, a decision has to be made. And if you’re not comfortable with conflict or disagreement, you’re going to stall. It’s easy to schedule another meeting, ask for more data, another what-if scenario. Or worse, calling in consultants or an agency to help. Unfortunately, the cost of delaying decisions in a startup is significant. And often employees will become exhausted trying to make their case in meeting after meeting.

Moreover, if the executives are slow to make decisions, that sets the example for the rest of the company. Decisions that could be made in hours or days get drawn out over weeks and months.

This is one of the reasons disagreeability is sometimes necessary. As an executive, you get paid to make the hard decisions, even if it’s not the popular or easy decision. You have to steel yourself and recognize that making decisions quickly is important. The sooner decisions are made, the faster people can get back to work implementing decisions instead of analyzing, presenting and debating.

When in doubt, think of yourself as a consultant to the firm and ask yourself what decision you would make if you were not hampered by the desire to please everyone?

In a startup, you never have perfect information. Instead, you must be ready to make decisions with sufficient information in a timely fashion. Waiting longer to make a decision often leaves people blocked from doing their work.

Ask yourself, can you make the decision today? What would be the downside of doing so?

Of course, you should also be able to explain your decision and frame it in terms of the objectives and values of the company. Making decisions quickly with the best interest of the company in mind will be respected, even by those who disagree.

As a manager, your goal isn’t to be liked. It is to be respected. That respect is earned by being transparent in your communications, clear about objectives, fair in evaluating people, and making good decisions. Managers who are too needy will find themselves neither liked nor respected. And without a clear objective framework, their decisions will be worse.

Listen More

As leaders rise in an organization they develop great skills as speakers. They give speeches at conferences or on podcasts, skate through interviews with press and analysts, paint visions of success for investors and motivate their teams to do great work. This is all part of being an executive. But sometimes, they get so used to speaking they forget the most important thing: listening.

Often executives get brought into customer meetings to speak to the strategy, the product roadmap, give their insights into the industry and perhaps the history of the company. Those are important topics, for sure.

But the more an executive is talking, the less they are listening. This is especially true of founders, CEOs and CTOs. The audience may be in such awe of their past accomplishments, that they go along with whatever vision has been communicated. Sometimes that means they are swayed by the presentation and buy-in full-heartedly. Other times, it might mean they don’t raise questions or objections.

It is exceedingly rare executive who has the gift for listening to customers. And yet, it’s the only way to ensure that you are building products that resonate with the market.
There’s a certain amount of BS in the tech industry that emanates from the Steve Jobs view of the world that customers don’t know what they want. Henry Ford was famous for saying that if he asked customers what they wanted they would have said a faster horse. Unfortunately, most founders and executives are not Steve Jobs or Henry Ford. Most executives would do better with at least 50% more listening than talking, whether with customers or employees.

For certain highly technical products, it’s fair to say that customers might not know the best architectural solution to their problem. However, customers are experts in understanding the problems they have and which problems are a high priority and which are not.

Many marketplace failures stem from interesting technical solutions to problems that customers don’t have or don’t care about. Asking open ended questions and listening are the only way to understand their needs and priorities.

Executives who profess that customers don’t know what they want are demonstrating contempt to the very people who pay their salaries. Not only does this risk product failure, but it can also result in a culture of arrogance.

One of the most impactful things I did at Duo Security was take what was a somewhat disconnected product team and get them out talking to customers. I set objectives for them to meet with 2 customers per month, each, which was more than they had done in the prior six months. In fact, they hadn’t talked to any customers. I helped them create a structured set of open-ended questions to uncover the problems they actually cared about. The savvier people on the product team made friends with their sales colleagues to get in front of customers, learn what they could and then shared the results across the entire engineering team. And while there was sometimes a level of panic that certain planned features did not seem to solve problems the customers cared about, over a few short weeks, we were able to re-orient Engineering toward the problems that really mattered.

Subsequent to this, we routinely invited customers to speak in person at our all-hands meeting, where they were interviewed on stage by our head of customer success. Customers explained what they liked and what they disliked about our product. Some came with a set of features they wanted to see in future product releases. I saw engineers hanging off every word from a customer who complained about the amount of retraining required for his users based on what had seemed like a fairly innocuous user interface change. Engineers talked about some of these customer interviews for years afterward. It truly reshaped the culture to become hugely customer centric, a trait that was a significant advantage for us in the market place. We no longer had to guess whether a new release would be successful or not. We were validating features with prospects and customers before we shipped.

I have never seen a company fail because it listened too much to customers. But I’ve seen the opposite many times.

As an executive how often do you listen to customers? How do you share the lessons learned from customer success and sales more broadly in the company? How can you make customer focus a bigger part of the culture?

Let me know your feedback or questions by posting a comment below. 


Zack oaxaca beer

I've started a new blog called Build To Scale that takes over from earlier writing I did about open source businesses. This is intended as a guide for founders and startup executives to help them build and scale a high-performance business. I will be building on lessons learned over several decades helping to build and scale companies like Duo Security, Zendesk, MySQL and Active Software, companies whose combined value grew to more than $20 billion. 

Some of the topics I will cover include:

  • Finding product / market fit
  • Fundraising
  • Building a high performance culture
  • Managing objectives
  • Scaling sales and marketing
  • Managing engineering
  • Managing through a crisis
  • Mergers & acquisitions

It's not easy to build a business and I am grateful to those who helped me along the way. Many of these lessons have been learned the hard way, and I hope that I can help founders and startup executives avoid some of the most common (and painful) mistakes. It's the kind of friendly but real advice you might get talking over beer or coffee at The Great Startup Bar & Grill, if there was such a place. 

Feel free to let me know questions you have or topics you'd like to see covered. Shoot me email (I'm easy to find) or add a comment below.  These posts are also available on Substack.