“What can you do about holdouts, or stubborn people on your team who don’t want to change to a different way of working?”


People resist change for different reasons. The best way to persuade someone to change is to determine their underlying motivations. To do that, we need to spend 1-on-1 time listening. Sometimes you may face resistance from a group of people, and in that case you’ll want to spend 1-on-1 time with the influential people in that group—as many as you can.

Don’t hide behind a mass email or a powerpoint talk when getting to the bottom of resistance. Instead, set up a 1-on-1 chat with each individual in a place and with a setup that lets them know it is psychologically safe to be fully honest with you. When someone knows you are genuinely trying to understand them, they will already be more likely to go along with the change you want. But if that alone doesn’t persuade them (and it often won’t), try to determine if they have any of the following common underlying concerns:

  • They don’t truly understand what you are trying to do.

    • Often people resist change because they don’t understand it. Check people’s understanding first before you jump to any assumptions. Gently ask them what they understand they’re being asked to do, and what questions they have about it. This will help you determine if you simply need to clarify things with them.

    • E.g. Say you have decided to get rid of your weekly team meeting. Some of your team might resist the change because they don’t understand how the team could function without a weekly meeting—perhaps because they don’t know that you’d instead like to have everyone email a progress report to you every Friday, and you’re also going to do a monthly team lunch so the team can still bond socially.

  • They disagree or don’t understand why you think the change is the right way to go.

    • Often people resist change because they don’t think it’s been thought through well enough. Well-meaning people want to do the right things in their work and on their teams. Resistance often melts away when we explain the process we went through to arrive at the conclusion we did. Even if someone ultimately disagrees with your decision, if they understand the process behind deciding it, they’ll have an easier time following along than if you just tell them “do it my way.”

    • E.g. Say you have decided to get rid of your weekly team meeting. Some of your team might resist the change because they don’t know that you did an analysis of the time-cost vs how productive the meeting was, and how much it would save everyone to instead do a weekly progress report. Showing the team this data might get them on board.

  • They think that changing will be extra work, and they don’t want to do extra work.

    • Few people like being handed extra work without additional compensation. So people will often resist change that sounds like more work. To resolve this concern, you can either a) convince people that the change will actually result in the same amount or less work in the long run, or b) convince people that the extra work will be worth it.

    • E.g. Say you have decided to get rid of your weekly team meeting in favor of a weekly report. Some of your team might resist the change because they think the report will be more of a pain than sitting in an hour-long meeting. Here you might illustrate to them an example of a report that takes less than an hour to do; or you might explain to them that because they can do the report on their own time, they can fit the work into their schedule more flexibly than a fixed-time meeting; or you might persuade them that this change will help the team run so much better that in the long run you will all be more successful—and recognized by the company.

  • Their personality is generally one of questioning and rebelling against external expectations.

    • Some people in your team may have different personalities than you. So it’s important to figure out if someone’s default attitude toward change is generally more skeptical than yours. And if so, don’t punish them for their personality. Instead, if someone is naturally rebellious, you’ll want to frame the change you’re asking them to do in terms of choices that they can make. Give them the option of choosing to not do what you’re asking by a) telling them what you’re trying to achieve, b) telling them how you’d prefer they change in order to help you achieve it, c) telling them it is absolutely their choice to comply, d) laying out the consequence if they choose not to, but e) telling them that if they can come up with a different way for them to help you achieve what you’re trying to achieve with this change without disrupting everyone else on the team, they are welcome to propose it to you. Sometimes you won’t be able to accommodate the resisting person’s preferred way of moving forward, but by giving them the choice, you’ll often win rebellious personalities to your side.

    • E.g. Say you have decided to get rid of your weekly team meeting in favor of a weekly report. One member of your team tells you they don’t like to be told what to do, and that they think reports are dumb. You might tell them that your goal is for the team to be able to share information asynchronously rather than in real time, and that you need to know what they’ve accomplished and planned each week. So if they can think of another way to get you that information that doesn’t involve a weekly meeting, you’re open to hearing about it. Otherwise, it’s their choice to either do the report or find a team environment that works better for them—and you won’t be offended in either case.

  • They have seen change initiatives come and go, and don’t believe that this one will last.

    • It’s easy to become jaded when leaders in the past have introduced “flavor of the week” initiatives, or when they haven’t pulled through on promises of change in the past. The best way to get past this concern is to persuade people to give your change an honest shot, promising them that you’ll periodically check in with them personally to assess if both you and they are holding up your end of the agreement to pull through. If at any point you (the change initiator) or they (the reluctant party) is found to not be putting in an honest effort, you can establish up front that such a scenario will trigger a conversation to resolve the specific concerns.

    • E.g. Say you have decided to get rid of your weekly team meeting in favor of a weekly report. One member of your team who has been around a long time has decided to hold out and wait for the new initiative to die. Sensing this, you can have a 1-on-1 conversation with them and extract a two-sided promise to give the new change a 1-month trial. You’ll check in after a month to assess if both you and they have given it the effort you’ve promised. If you as the leader cannot keep up with the reports as promised, you will involve them in coming up with a new plan. If everyone holds up their end, and the initiative doesn’t work, you’ll still involve them in coming up with a better solution. And if they do not hold up their promise to give the reports an honest shot, you’ll discuss why not, and whether it makes sense for them to work on another team somewhere else.

  • They think the change will conflict with their own priorities or add unequal pressure on them vs others.

    • Sometimes asking people to change will put them in a position of newly competing priorities. In these cases, you need to be prepared to justify why it is worth it to the broader team for you to put undue burden on them—and you need to do your best to align the priorities so you don’t put your team members in impossible situations. In many cases, these kinds of concerns will actually unearth perspectives and information that will help you adjust your own plan to be better—so be open to this.