How Can I Convince My Team to Try Something Different?

Advice from The Sherwins for November 2017

Convincing My Team to Try Something Different


Hey Sherwins, I need your help.

I am a product manager who recently started working with a team of engineers. They have been together for years, struggling to improve a widely-used legacy product riddled with technical debt. After engaging with stakeholders, I found multiple ways to provide existing value and new value to an upcoming high-growth area for the company using radically different technical approaches. All of these options would require a year of dedicated rework, but I believe that I can convince company leadership to make the investment.

My challenge is that I can’t convince my team to even discuss the possibility of doing something different than what they have been doing. My attempts to sell them on the opportunity and company benefit have failed. I have dealt with individuals with this sort of closed-mindedness in the past, but never an entire team.

Have you encountered teams like this before? What should I do?

Warmest regards,
PD in Texas


Have you had a meeting where you don’t discuss your own plans? A meeting where you just find out what’s happening? Have one of those. If you’ve already had one, then have another one. Before the meeting, make a list of questions to obtain the following information: What each person is doing, where the product is going, and how their work contributes to that. These are not personal questions. These are not individual visions for the future. These are not problems to be solved. You’re looking for project deliverables, outcomes, data, metrics, roadmaps, real live things. All of the ways that your team knows if they’re successful. Ask everyone at the meeting the same questions. Have each person put their answers on a whiteboard. Let the team answer and build the picture for you. Let them figure out how to tell you and show you what’s happening right now and where things are currently going. They’ll be contributing individually to a common thing. You bring the questions, they bring everything else.

At the end of that meeting, you will have a pretty good idea of what the plan is. For now, let’s call it the Pizza Plan.

You’ve got a vision for how this team could function and what this product could be. For now, let’s call that the Salad Plan.

In order for this company to adopt your Salad Plan, you want a year of rework from them.

That’s a bold ask, friend.

You just started working at a company with an established, recognized product, which already puts you in rarefied air. Hundreds of startups will be born, sputter, and die before your company will even have to think about a refreshed logo. And it’s good to remember that the legacy pizza  you’re suffering under right now was compelling enough to pull you in the door and inspire you to plan big plans. Does your team know that?

Your team makes a choice every day they walk in the door. Every single day they are following the Pizza Plan. So you need to acknowledge that, and your team needs to acknowledge that too. Out loud, in writing, whatever: Every day we do Pizza.

You aren’t *not* choosing or feeling helpless and frustrated or waiting until that non-Pizza Plan campaign starts. And you, as the product manager, have to acknowledge the Pizza Plan in a positive and supportive way. Not in a chipper, fake-positive way, but in a way that is accomplishment focused rather than problem-to-be-solved focused. You’re asking them to change before you’ve proven you can support them through that change.

It’s clear to you all of the things that could be better. And that’s inspiring. It’s great that you have a long-term, complete vision for your team and for the product. However, convince is not the word to use. We have a hunch why you’re having so much difficulty when you’re broaching the subject of change. You’re likely setting it up so that your idea is the right one. You’ve framed the problem and you’ve got the solution. You’re done with pizza and your team should be too. This is understandable; It’s usually not good form to come without a complete argument. But you might not be doing enough work to acknowledge what the Pizza Plan is currently accomplishing.

Organizationally, it sounds like you’re working with a clan, and clans make decisions together. It’s really difficult for a single individual to change the direction of a clan. You have to find out what they want, and saying to yourself or to anyone else, “Well, they sure as hell don’t want the Salad Plan.” isn’t going to help you. It will curdle your relationships with them. It will make you unable to support them, even when they do dumb things, which is what a good PM does in a clan—they support the team even when they choose to do dumb stuff.

With a clan, if the ship is going down, you go down with it. Loyally. Publicly. Enthusiastically, even. A clan PM brings the team to the table and says, “Ok, Pizza didn’t work. Now what do we do?” You have to respect their decisions, with your voice as an equal part of it. You don’t get more of a say just because you’re the throat that management gets to choke. No PM ever gets to say: “Time for a year of salad, bitches!”

We’re not saying clans are the best environments for great products. But that’s what you’ve got to work with. Because here’s the tough part of all of this, clan or not. When you’re trying to convince your team to change their ways, to change the Pizza Plan, you’re inadvertently asking the team to admit that what they’re currently doing sucks. People don’t look at themselves in the mirror and say, “Today, I will do inferior work!” And only a poor craftsman blames his tools.

If the team says things are too difficult, don’t ask what you can give them to help. Instead, say, “From the information that I have, the team is capable of doing X. Tell me where I’m incorrect.” Allow your team to build with you. And be specific about the X. Don’t punt and say something lame like being successful.

Having a vision, rallying the troops, imagining a brighter future, all of that lingo hides within it a shaming of the status quo. And within that shaming is a shaming of our time, a shaming of the reasons why we get up in the morning and go to work and fall into bed at night tired with our effort.

For some, to be constantly improving is a beautiful and inspiring thing. But if you want to improve, you must first be dissatisfied with what you have. Vision does not come from satisfaction. To dream means to see a hole, a lack, a hunger. Right now, you are trying to make your vision their vision by expressing dissatisfaction where there may be none. Not everyone likes to be told that they need to improve, and not everyone will want to improve on your terms.

By finding out what the Pizza Plan is, you’re also learning their terms. How do they express disappointment? Where are they feeling hunger? Did they get to where they are through action or through passivity? When will they know they are successful? You have to tell them your assumptions around one of your ideas and let them show you where you’re wrong before you can start rebuilding the Titanic.

In other words, stop trying to see, define, and solve problems without your team. The best idea in the world isn’t going anywhere unless your team is a part of it. Otherwise, it’s always going to be PD’s Idea, and they’ll just be the people who helped you help the company make more money.

We’ll send you on your way with that, PD. But we’ve also got something to say to your team.


Hi, Team.

We’re going to assume that you all aren’t coasting along until you hit retirement. We’re going to assume you’re competent at your jobs and that you don’t need to be told to find another place to work.

PD tells us that you don’t want to change things. Which you probably don’t. That’s fine. Maybe PD’s trying to cross the river to get water, so to speak.

However, after a while, legacy products and their seemingly unending technical debt and backlogs make us task-oriented, putting out fires, checking to-dos off a list in order to finish a sprint. They make us weed pullers rather than stewards of the land. We get tired, and we lose sight of the vision that launched our product in the first place. We say no to new ideas because we want to protect our product. We say no preemptively, because we know better, because we’ve got all of these weeds to pull and we don’t want more. We’ve finally got things working well and we don’t want to mess it up. And we forget how much has really changed since the day the product launched. And that things are going to continue to change.

One truth in tech: You learn to swim or you’re taken by the flood. Are you going to claim those changes as your own, or are you going to let others inflict them on you? Don’t choose PD’s plan. Make your plan with PD. It is your vision, your product, your choice. Together.

The move from saying no to saying yes to something else is a big one. But consider that Hammarsköld quote: “Life only demands from you the strength that you possess.”

Be strong, team. Choose your path forward. Don’t let it be chosen for you.

The Sherwins


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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. This advice will only be on the Internet till November 30th, 2017.