10 Reminders When Weathering Change as a CS Leader

10 Reminders When Weathering Change as a CS Leader
Brett Matthews

Last December I started a new Manager position within Customer Success at Microsoft, building a CS Team within the West Enterprise.

I had to quickly not only onboard myself with a myriad of tools and processes, build and merge two teams, think and plan for account coverage, and most importantly build relationships with a new team with varying degrees of tenure ranging from Day 1 to 20 Years. Coupled with new contracts coming in, coverage for accounts, revenue growth and delivery excellence.

Flash forward to today. Seven months later and start of the New Fiscal: More Changes, which leads me to Weathering Change — The Top 10:

1. Turn and face the strange.

The Pandemic was a great reminder of the benefits of keeping agile and facing the unknown. The ultimate biproduct was an incredible resiliency. I applaud each and every one of you. Disruption was knocking at every doorstep and employees had to reinvent not only how they work, but diversify entire business lines to keep afloat.

May we look no further. No one knows how to change more than Bowie himself.

David Bowie Meme
David Bowie Meme

2. Keep the big picture in mind.

We all get stuck in our ways. We all get attached to our people, our org charts, our managers, and our customers. And why shouldn’t we? For most, change disrupts our inner well-being, confronts who we want to be when we grow up, and for some white knuckle pretty much everything.

Change requires basking in the unknown. When you're in the midst of it, it can feel a bit like the left side — a ball of knots of tools, processes, and people thrown together from management that will never align.

Ball of knots

But change agents and advocates, focus on the right side and trust for cleaner, smoother water, and better direction ahead. Stay focused on the long-term vision or broader purpose.

3. Live in present and future.

Great leaders do this, and most don’t even realize they are doing it. They dovetail seamlessly between present and future, connecting immediate needs and aligning to long term vision. To lose sight of one is to lose sight of the other. If we focused just on the short term, there would be no long term. Peter Drucker the godfather of change, recommended that at least 10–20% of an executive’s time and resources be spent on the future.

“Management…has to live always in both the present and future. [It] must keep the enterprise successful and profitably in the present — or else there will be no enterprise to enjoy in the future. It must simultaneously make the enterprise capable of growing and prospering, or at least surviving in the future — otherwise it has fallen down on its responsibility.”

Peter F. Drucker

4. You play a critical role.

This is often a forgotten one. Too often we think we are only the recipients of change. When the reality is we play a critical role: we own the change, the success of the change, and the culture that embodies it. Organizational change is an opportunity to help your organization succeed and to show you have a growth mindset. It’s also an opportunity to take a leadership role and help others; it can help your career in helping people make the transition.

5. Transparency helps.

With any change, people have to be brought along for the journey. The What, Where, How, and Why become critically important. Communicate early and often and walk individuals affected through 1:1s. Timing can have multiple dependencies so it’s important to think about the effects, as well as draw in feedback. “What have we not thought of?” Can go a long way.

6. Change is growth.

Way overused, but it is an opportunity to expand your network, garner support outside of your own organization, work and expand reach with others, or take on new projects or customers.

7. Keep in mind what’s not on the slides.

This is usually what’s not on the org chart, the boxes, or just ignored. People are people. And usually what makes them go are relationships. It’s important to think, consider, empathize, as well as allow for grace on how new teams need to be built.

Sean Conner’s illustration of Bruce Tuckman’s team model.
Sean Conner’s illustration of Bruce Tuckman’s team model.

8. If you don’t like it, just stay and it will change.

I used to have a manager wise beyond his years who told me, “Don’t like it, just stay, and things will change”. Truer words never spoke. See #1. Remain Fluid.

9. Allow room for the unknown.

Will everything be perfect? No. But don’t let perfect get in the way of good or even great execution. Allow ideas to percolate and have a place to capture them. One could turn into gold.

10. Change is constant — life is a journey.

Customer Success is a journey. You are a journey. So let your organization be a journey and hopefully you get a real strong chance to be an enabler. Embrace and enjoy the ride. Maybe we can even be heroes just for a day.

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