The Lightning Round

Advice from The Sherwins for October 2017

The Lightning Round


We’ve gotten a lot of letters over the past few months, and we’ll never have enough space to answer them all. But we have to try, right?

—The Sherwins


Should I quit my job?

Yes. But as a good friend says: “Run to, not from.”


How can I enhance the process of performing a competitive analysis?

Enhance? Like, with lasers? With drugs? Or do you just mean, “get more useful information out of a competitive analysis”?

Ask yourself if you actually want to be competing with the companies in the analysis, and write down the reasons why or why not. Everyone seems to skip over this part, and it’s baffling. Without this information, you can’t contextualize any of your data. If you don’t know that you want to go head-to-head with Company B because of this particular technology that you’re both chasing, then you won’t see Company J as a threat until they’ve bought you.


I’ve been asked to work with a client that goes against my morals. What do I do?

Talk to your manager. If nothing changes, or no one can find a way for you to avoid being on that project without incurring punishment, find another place to work. We are totally not kidding about this. Do not put your soul in a drawer, not even for a day, for work you can’t stand behind.


I just started a new job, and I was told I should observe what’s going on for at least four weeks, but it’s clear in just two that there are some major issues that need to be dealt with. If I don’t do something, I can’t imagine the damage that could happen in the long term. If I’m responsible for what’s happening right now with my team, how much should I assert myself with the folks I’m trying to build up trust with?

Told by whom? Go talk things out with that person first. Then worry about the company exploding and trust issues. We think there might be more to this story. And also, the number of companies that we know of that exploded because of a decision that a single new non-CEO hire didn’t make in their first four weeks is < 1.


Our company is finally transitioning to Agile. What’s the biggest mistake you’ve seen Scrum teams make?

Blaming the process. We’re all grownups.


I’m clearly not part of the inner circle at work, and it’s preventing me from getting my job done. How do I do what I was hired to do?

Inner circle? Are these the same people that want the enhanced competitive analyses?

You wouldn’t have been hired if they didn’t think you would fit or be able to do your job, right? Our question to you is: What do you actually need to get your job done? If you decide to not spend half your paycheck getting high with your coworkers, how exactly are things not getting done when y’all come in for standups? If you want things to change, you have to start with behaviors.

But let’s go right back to your question: You have a job where you have to be part of an inner circle in order to get things done. That seems to be the answer to your question then. Be part of the inner circle. Ask yourself if that’s what you want. In order to do your job, do you want to be part of the inner circle? If not, then you should find another place to work. Why? Inner circles eat their own.


My company just laid off a bunch of people, and because I’m in management, I know that things aren’t looking good. The company has really changed since I started and I’ve wanted to leave for a while, but now I feel like I should stay and support my team…

Do you make a product that saves people’s lives? Then stay.

If not, you need to leave. Have a time frame, and two or three tangible goals that you want to accomplish before resigning. You’re sticking with a company that you don’t really believe in because they’re having a hard time. Well, your company isn’t your boyfriend. You aren’t supporting your team by showing them that it’s okay to compromise your principles. Support your team by showing them how to exit like a professional.


Things keep changing at work and I’m sick of it. I think we just had our fourth reorganization in 18 months. This is frustrating, because I think we have a great product and when I talk with customers, they rave about what we’re doing. But if they could look under the surface, they’d see us running around with new managers and constantly changing projects. Is this normal? Should I learn how to deal with this, or find a place where things aren’t in chaos?

First off, stop worrying what will happen if the customers find out. Unless you’re at Uber.

Reorgs are rarely popular, because the C-suite never manages to accurately describe what the reorg is trying to accomplish and what problem it’s solving. Most reorgs cost more money than they save, because of about fifteen completely avoidable mistakes. If your company’s had four in 18 months, they are doing it wrong. So, to answer your first question: No, it’s not normal.

Many good designers have gotten lost trying to climb “But It’s a Great Product” Mountain, never to be heard from again. So, we’ll leave you with these questions to ponder:

  • Can you separate the product from the people who dedicate their lives to making it real?
  • Would your company treats its customers the way that it treats its employees?
  • Is a product that comes from a bad company still good?


Should I work with a friend on their business?



But you two are friends, right?

Yes. But you still shouldn’t do it.


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Send questions to questions (at) askthesherwins (daht) com. All questions become the property of Ask The Sherwins, LLC and may be edited. Our advice shouldn't be construed as a replacement for the appropriate legal or professional counsel.