“I need you to be more strategic."

This is harsh feedback to receive as an employee, whether you're a manager or an individual contributor.

What does it even mean?

A quick google search of how to be more strategic yields over 2 billion results, and the top results all focus on being a more strategic thinker.

While thinking is certainly part of being strategic, it's a bit like talk with no action... it's cheap.

I firmly believe that strategic leadership is a function of both thought and behavior. Demonstrating strategic behavior will grow our influence, build our reputation, and help us achieve our goals.

Some people are naturally strategic, while others have to work at it.

But I believe it’s a muscle everyone can build over time with practice.

To that end, here are seven behaviors that customer success leaders can adopt to become more strategic.

1. Do what only you can do

Years ago, I had a customer support director who reported to me.

This person had a large team of support reps reporting to them and was also terrific at handling the most demanding problems customers could throw at us.

I rested easy knowing they handled our most complex cases properly.

But there was a problem. Our processes and quality of execution weren't improving. We were stuck in a scalability rut.

It’s almost always easier to do things yourself versus enabling others and building scalable processes.

After all, given our experience, we can often do a task faster and with higher fidelity than our teammates, right?


There are two problems with this approach.

First and most obvious, you can’t scale as a leader if this is how you work. How will you have time to solve more complex problems if you focus on work that someone else can (and should) do?

Second, it stunts the team's growth. Most of our companies will be 10%, 20%, 50%, or 100% larger next year than we are today. Therefore, we need most of our current team members to handle 10%, 20%, 50%, 0r 100% more complexity next year than they are handling today.

How can you take the business to the next level if you're keeping all the difficult work for yourself?

We must delegate.

But delegation isn't the end of our responsibility. As leaders, we are accountable, and our role in achieving outcomes changes.

Instead of doing a task ourselves (the tactical approach), 0ur role is to set direction, set expectations of quality and timeliness, routinely inspect progress, and provide real-time feedback and coaching.

I often ask my leaders in our one-on-ones, "What work are you uniquely qualified to do, and what are you doing today that you should delegate to your team?"

Delegation is a strategic behavior.

What are you holding onto that you need to give up as a leader?

2. Be specific about the problems you're solving

I wrote a longer piece on customer success strategy a couple of weeks ago, and I won't regurgitate it here.

But we must tie the activity of our teams and the projects we undertake to desired business outcomes.

I’ve seen countless well-intentioned customer success teams run into trouble by tying their work to fluffy goals like "improving the customer experience" and "building deeper relationships with customers."

While these are noble goals and likely outcomes of our work, we must never forget that we're a part of a business with a P&L. The most significant expense any software company carries is its people (further proof that these are people businesses!).

We need to explain how CX and relationships affect the business, i.e., increased growth, better retention, or lower costs.

Strategic leaders routinely step back once a quarter to evaluate their team's activities and impact, answering the following questions:

  • What are the top opportunities/challenges we are solving?
  • How are we going about it?
  • Is our approach working?
  • Are we making fast enough progress?
  • Is there a better way?

Which initiatives do you need to reevaluate as you plan for 2023?

3. Pursue simplicity

“Everything should be made as simple as possible, but not simpler.”

- Einstein

When I joined Higher Logic, I went on a listening tour and captured large amounts of feedback from our employees, partners, and customers on what we were doing well and where we needed to improve.

The amount of data was overwhelming.

As I aggregated it, several themes emerged, which we turned into pillars of our strategy, which became the following:

  • Engage - Proactively deepen our relationships with our customers to assess their health and drive net retention.
  • Support - Be reliable when our customers need help.
  • Renew - Develop operational excellence around renewals, a leading indicator of net retention.

For the first 18 months, every initiative we took fell underneath one of these pillars.

We created programs that allowed us to engage with our customers on a proactive basis and at scale.

We improved our customer support experience by adopting new processes, upskilling our teams, and monitoring quality.

We even created a specialist renewal team and developed a playbook for driving retention during the initial COVID-19 recession, which hit our customers hard.

We organized dozens of sub-initiatives and thousands of tasks into a simple framework tied to business outcomes. This framework simplified how we communicated our plan to the team and the board.

This approach works similarly no matter the level we're working at, be it company level, within an individual team, or even as an individual contributor.

How can you simplify your work to help others better understand it?

4. Seek wise counsel

My CFO has the gift of discernment.

When I bring ideas and plans to her, she asks questions that help me see around corners and flesh out details I've overlooked.

I’ve grown to rely on her ability to ask me simple questions that cut straight to the heart of a matter.

We should all be lucky to have two or three people we can rely on for counsel, and strategic leaders seek them out to socialize plans and get feedback.

Who are the wise counselors that listen objectively to you and ask challenging questions that help you refine your approach?

5. Drive alignment

“Have the meeting before the meeting so you don’t have to have the meeting after the meeting.”

Early in my career, I used to get ahead of myself (hell, sometimes I still do).

I’d come up with a fantastic idea and jump into execution mode.

I didn’t realize at the time that I was missing an opportunity to rally people and drive the support I would need to bring that idea to life.

As my career evolved, I realized it was worth my time communicating new concepts in one-on-ones and small groups before presenting them to the broader team.

Does it take more time to do this? Yes.

Does it seem less efficient? Yes.

Does it save time and heartache in the long run?


As I was researching this post, I ran across a framework called Two up, Two down, Two across, which I like (see the link below).

It’s a pretty simple idea that helps you map your strategy to the rest of the organization:

  • Two up - what is your boss’s boss trying to achieve? If your boss is the CEO, two up represents the desired outcomes of your board of directors.
  • Two down - what impact will your plans have on your team two levels below you? What communication and enablement will they need as you move forward?
  • Two, what is your plans' impact on peer lines of business in your organization?

Strategic leaders identify and plan for the needs of those around them, up, down, and across the organization.

Whose jobs may change, or whom do you need to buy into for your plans for them to work?

6. Execute to learn

We would all love to have data to back up every decision we make, but this is seldom the case in the real world. Leaders often have to move plans forward with incomplete information.

This fall, we embarked on a mission to restructure our packaged professional services offerings, and there is one offer we can't quite get our collective heads around.

Instead of contriving something we thought would be right, we launched the service to a few pilot customers to see what we could learn.

To drive momentum, we decided to work in two-week "sprints" (any agile practitioners out there?), beginning with crafting a pitch deck for the service and taking it to a sample set of customers to get live feedback.

Great is the enemy of good. And outside-in feedback and data are better than our hunches.

Strategic leaders understand what they don't know and devise a plan to gather insights quickly. Then they use those learnings to guide their next steps.

What’s the smallest test you can run to get the insight you need to develop your plans further?

7. Build relationships before you need to lean into them

It takes many different types of people to run a technology business.

Sales, engineering, marketing, services, support, product management, finance, etc., and that list represents virtually every personality profile under the sun.

As much as we think we’re in the technology business, we aren't. We are in the people business.

In the people business, trust becomes the currency of success. Therefore relationships underlie everything we do.

It’s our job as leaders to bring this motley crew of personalities together around a common goal: making customers successful and, in turn, realizing our businesses' growth and profitability goals.

The best leaders know that having cross-functional relationships before conflict arises puts you in a better position to succeed when difficult situations and complex projects demand collaboration.

How are you intentionally building relationships with the people who lead these areas in your company? What cross-functional relationships do you need to develop as you prepare for 2023?


Being strategic is all about action, not just wide-aperture thinking. If all of this sounds like difficult work, you’re right; it is. But when we choose strategic behavior, we waste less energy, move faster, build more credibility, and improve outcomes.

And that's a recipe for career growth.

What strategic behaviors will you adopt as you gear up for 2023?


💡 Weekly Favorites

Here are some of my favorite podcasts, blogs, and videos from the week:

See you next Sunday.