How To Lose Customers & Alienate People

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Founders and CEOs are sometimes accused of being out of touch. If that’s your goal, here are seven tips on how to get there faster.

Don’t Listen, Just Talk

Talk to customers, talk to employees, talk to customers. The more you talk, the less you have to listen. Give them your vision, and heap it on with lots of diagrams and charts that explain the architecture and how powerful it will all be. You’ve thought it out and most of it is working and by golly customers are going to like it. That is, if you ever get around to shipping. Sorry, there’s no time for questions.

Shoot the Messenger

No one likes bad news, especially CEOs. So, why not just eliminate it? Next time someone raises bad news, unload on them in public. The more junior the employee, the bigger the thrashing. Tell them they’re part of the problem. You’ve got an executive offsite coming up in a few months, and it’s not for them to worry about customers or quality or whatever it is they’re complaining about. And when an employee makes a mistake, yell at them. That’s the best way to motivate people so they stop sharing bad news. Or any news.  

Obsess with the Competition

Let’s face it, the biggest idiots out there are your competitors. Sure they launch cool products, but so what? It’s all a bunch of marketing BS, right? Who cares about that? And that feature they implemented is just a copy of something you thought about years ago. Celebrate every outage they have as if it’s some grand accomplishment from your team. That way you don’t have to think too much about all the things you haven’t shipped.

Raise More Money

One way to make sure you’re out of touch is to spend more time with investors than customers. That way you can talk about strategy without having to worry about pesky issues like customer satisfaction, churn, employee engagement. And when those topics do come up, it’s just an abstraction like an NPS number or a survey score. Don’t get distracted by the people. Just think about numbers. Spreadsheets, right?

Hire Yes-Men

Yes-men don’t have to be men, but they have to be in agreement. All the time. You don’t have time for devil’s advocates. Or disagreement. Or discussion. If you need new ideas, you can always acquire another company.

Screw The Customer

Think of your customers as a captive audience. Sales missing the target? No problem, raise the prices. I mean, it’s not like they have a better option, right? If customers knew what they were doing, they wouldn’t have bought from you in the first place.

Focus on Optics

Perception is reality, amiright? So just focus on that. If you look good, maybe you don’t have to actually be good. Besides, how would it look if you changed now?

We all have our blindspots and occasional lapses of judgment. When in doubt, listen to your employees who listen to your customers.

The Power of Velocity


Running a startup can sometimes feel like hell. And as Churchill said, if you’re going through hell, keep going. Forward progress can be hard to maintain when there are customer disasters, technical setbacks, funding challenges and more. But what other option is there?

As a startup, making forward progress is essential. And if there is any competitive advantage a startup can have over larger competitors, it’s that it can and must move faster.

Let’s face it, most large companies, no matter how agile they once were, get bogged down. The more success they have, the more they grow, the slower they get. Middle managers are hired, rules are made, and new processes are created all in an effort to ensure that no mistakes are made. But those processes and the bureaucrats who create them also cause a side-effect of slowing things down. The culture that once boasted of moving quickly, becomes complacent and accepts that because there are more people, things take longer.

New competition? Let’s take a wait-and-see approach. Sales problems? Schedule a review at the end of the quarter. Need more engineers? Budgets have to be approved. New product idea? Surely that can wait.

Most startups move fast. But if you’re not careful, you can end up re-creating the same bureaucracy found in larger companies.

If you’re the founder, CEO or executive, you can’t make all the decisions youself. That will only result in slowing things down as a pile-up forms outside your office, your email in-box or your Slack DMs. So you must create a culture that empowers others to make decisions. And you must set the pace for making decisions quickly.

In an efficient startup that means if a problem is found on a Monday, you’re brainstorming ideas on Tuesday, picking the best solution by Wednesday, implementing it Thursday and measuring the results by Friday. That might seem optimistic for some problems. Engineering complex solutions might take weeks. But for many other problems in sales, marketing, customer service or finance, it should be achievable.

Startup leaders need to demonstrate the importance of velocity to their teams. There will always be a desire for more more input, more discussion, more research, more data, more analysis. But that must always be tempered against eroding the advantage of startup speed. And in truth, how often does delaying a decision yield better results?

In the early days at Zendesk, we faced significant competition from Salesforce who had acquired a smaller competitor of ours called Assistly. Assistly was priced cheaper than we were and appealed to very cost-conscious small businesses. We created a “never lose on price” campaign which gave our sales managers the ability to aggressively compete on price against Assistly and other low-end competitors. We trusted our sales team to not lower their price unless they had to. And we knew that by approving a price match in real time with the customer demonstrated our ability to respond quickly to their needs. We also knew that getting a similar discount app, a trial period extension, or other change from Salesforce would typically require three levels of escalation taking weeks inside of Salesforce.

It’s possible that we left some money on the table with customers who might have gone with Zendesk instead of the lower-priced rival anyways. But the confidence the sales team developed during this process, the momentum within the company and impact on the culture was well worth it.

As you grow your company, you will often need to develop additional layers of process. There will be board meetings, executive meetings, departmental review meetings, pricing committees, product councils, launch meetings, and a myriad of short-term task forces. In all cases, these processes will be set up to generate better decisions, or more transparency, or higher collaboration, fewer surprises.

However, if you’re not careful, meetings and processes may end up bogging down decision making and watering down accountability. So whenever you define a new process, be clear on who owns the decision and when it will be made. And at any point if you are reaching the point of diminishing returns from these meetings, ask that the decision gets made immediately.

If a process or meeting has outlived its usefulness, don’t be afraid to disband it. This is especially important as you bring in new managers or executives. Give them the opportunity to eliminate the bureaucratic processes of their predecessors by paring back the number of attendees or scope of meetings.

As you look across your organization, are there decisions now taking longer than they should? Are there too many layers of approval? Is there confusion about who makes the decision? What steps can you take to cut through the layers so that speed remains a competitive advantage?

Let me know your thoughts by posting a comment below.

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.