Making Change without Breaking Things: Ask Madeleine

Dear Madeleine,

I am the CEO of a mid-sized business. I was the COO for many years and stepped into the CEO role six months ago. The good news is that the business is in good shape—there is a high demand for our products. The bad news is that it could be so much better.

Our former CEO was a bit technophobic and totally risk-averse, so he resisted my efforts to upgrade things when I was COO. He knew he was stepping down, so he figured I could just do what I wanted when I took the CEO job. But he left me in a bit of a fix. All of our systems are antiquated to the point that some versions of some software are no longer supported by the developers. Literally every process and system we use needs to be overhauled. Some can be consolidated with new software and some can be eliminated.

I am getting an endless stream of reports, many of which are incomplete or simply irrelevant. I worry about how much time is being wasted by the people who create them. My current leadership team is? mixed—some are as frustrated as I am and expect me to fix things fast, and some don’t see any need for change and are worried about my urgency.

I have a big vision for what is possible and feel a lot of responsibility to bring us into the twenty-first century, late as it may be. As I said, the business is in good shape, but that isn’t going to last if we don’t up our game.

My question is: How much is too much? How fast is too fast? How do I go about making change without breaking things beyond repair?

Where to Start?

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Dear Where to Start?

I can feel your commitment and your frustration. If I am understanding you correctly, the question actually is: How do I prepare the business to be competitive in the future and ensure its longevity without disrupting its current success?

It would almost be easier if the business were already showing signs of distress caused by the lack of modernization. But in most cases (as you well know), by the time that happens it is already too late. The problem is that people generally aren’t willing to change until the cost of not changing becomes unbearable.

I’m sure you wish you could wave a magic wand—but I’m not sure that would get you what you really want. Because the due diligence, research, coalition building, and other work you do to gain support for your vision will help you refine that vision and ensure that you get it right in the long run.

The first order of business is to articulate your big vision, craft a high-level strategy for how to achieve it, and get unequivocal support from the top. You don’t mention a board or owners, but presumably there are people who care as much about the long-term success of the organization as you do. You will need their support to do even a fraction of what you envision.

Then you will need a long-term plan. In this case, start with three years. Get input on the plan from your board, your leadership team, outside consultants who specialize in business transformation, and any other smart people who are willing to take the time. You probably have some smart individual contributors in the organization who see what you see. Get them involved.

Once you have a plan, share it with the entire organization. Once again, seek input. This is almost impossible in large organizations but there are ways to do it in smaller ones. There will be a lot of resistance—some of it short-sighted but also some that might point to flaws in the plan. Truly listen, don’t just act like you are listening.

Then go. Slowly, carefully, respond to concerns, talk to people, encourage them, and remind them what the point is.

You may very well have to replace some members of your leadership team. You cannot attempt full-on transformation without united leadership. This is tricky, because you also don’t want to surround yourself with yes-men. People who mindlessly agree with you are not the answer. You will want to encourage dissent and contrasting views and consider all viewpoints. Your leaders don’t have to agree with every change, but they do have to agree to support it once the team has decided on the best course of action. Without leaders who can inspire, role model new behaviors, patiently explain the why for any new change, empathetically talk people off the ledge when they are freaking out, and hold people accountable, nothing good will happen.

You also will want to be on the lookout for leaders who feel coerced and resentful, who say one thing to you and something else to their team. In the interest of keeping their jobs, they say yes to your face and then discredit you to others. They duck responsibility and blame the powers that be—in this case, you. They build their own coalitions of people who are loyal to them but not to the organization, which creates a hopelessly siloed organization with departments working at cross-purposes. These pockets of discontent in your organization will weaken it slowly in ways that will be hard to pinpoint. But if we agree that whatever is going on in any unit is about the leader, that is your clue.

The more work you put into planning, inviting input, re-designing the plan, and mapping out the steps to execution in a timeline, the better off you will be. Spend time talking to people and listening to them. Use a phased approach. It will take more time than you want it to, but trying to move too fast won’t get you the results you want. Be prepared for roadblocks and setbacks, and use them to learn and get better.

CEOs who manage turnarounds aren’t known for their patience or their empathy. And most get it spectacularly wrong.

Get support. Invite input. Win hearts and minds. Tell stories. Use examples. Communicate more than you think you should. Take it slow and steady, one foot in front of the other, one step at a time. Respond to new information as it comes in. Track and praise progress, take obstacles in stride. Reward persistence and grit.

Oh—and keep your sense of humor.

Love, Madeleine