How to Build a Coaching Culture: 5 Ways to Navigate Organizational Change

It’s easy to look back at 2022 and spot the big shifts in our industry, but recognizing how those changes affect our people and our sales cultures requires a deeper look. Last year, 40% of revenue teams experienced restructures, layoffs, hiring freezes, and other disruptions; as a result, 72% of revenue leaders say they struggled to hit goals or retain reps. This data tells us everything we need to know about the toll it’s taken on our sellers: they feel exhausted and discouraged, and rightfully so. 

The upside of this is that those people—the ones who feel unsettled and uncertain in the wake of such changes—are also the people who care about what they do and where they work. Those are exactly the kinds of people we want on our teams. How can we reignite team loyalty and love and emerge from change stronger than ever?

I recently sat down with Jen Allen, Community Growth at Lavender, and Shay Keeler, Director of Sales at Outreach, to talk about how sales leaders can better lead their people through organizational changes. And ya’ll, Shay Keeler said it best: “As a sales leader, you're kind of a therapist.” It’s our job to manage our people as much as we manage the numbers, and in order to do that, we have to embed coaching within our sales cultures. 

Here are 5 of the most impactful takeaways from our conversation that will help you create a coaching culture and guide your people through change with resilience, empathy, and confidence. 

What is a coaching culture?

Individual reps and teams need consistent, programmatic sales coaching to improve skills and become more effective in their roles. But there are secondary benefits of making coaching an integral part of your culture that go beyond the numbers. 

A coaching culture is an environment where questions are welcomed and where failure is seen as an opportunity to learn and optimize. By nature, 1:1 sales coaching builds relationships that result in smoother collaboration and problem solving, but also greater transparency and accessibility when it comes to navigating the inevitable challenges and changes we all face in the workplace. 

5 Ways to Create a Coaching Culture and Guide Your People Through Change 

1. Manage the person first, manage the numbers second

Anxiety, stress, and low morale are likely to creep in during times of transition, and rep productivity is bound to slip. Your people need space to process and ask questions before they can effectively return to full productivity. Use your 1:1 time to get to the heart of how your people are feeling. Be a listener, remind them that you are navigating the change together, and answer the questions you can. When a coaching culture is in place, you’ve already established a safe environment for uncertainty. You don’t have to have a solution all the time. Part of your job is to listen and validate. 

Source: Lewis Leadership

“Oftentimes people just want to be heard and understood, and that is so very different than managing the mechanics of a business.” – Jen Allen

2. Re-align on values

Values serve as the backbone of culture. When you’re going through a tough time, personally or professionally, it’s important to remember your “why.” What is the greater mission and purpose that drives your work? What are the values that ladder up to that mission? And, in the midst of change, do those values still apply? Maybe your values need a refresh. In order to maintain a culture that helps carry everyone through transition, get your people involved in redefining and shaping those new values. They’ll feel a sense of ownership and renewed purpose. 

“It’s really important to not just tell people what the values are, but to involve them, get their feedback, and get their thoughts. It’s constantly evolving. What things looked like at the beginning of the year may look different by the middle of the year, so we have to constantly evolve and make changes.” – Shay Keeler

3. Don’t make assumptions

We can’t make assumptions about how people will respond to big changes like growth, restructures, and new leadership—and we can’t fall into a groupthink mentality and expect others to communicate the right information or next steps. Show up, make time, and be available for your people. Waterfall the information you get down to them when appropriate to provide context for what happens next. Constantly provide opportunities for people to ask questions. This reminds them that you care about them as people first and will build greater trust. 

“We make all these assumptions that people will just get it and figure it out. We need to treat people like adults, have hard conversations, and also make it accessible for them to understand: how is this going to look and feel differently? So when it happens to them, they’re not completely caught off guard.” – Jen Allen 

4. Find your champions

Even if you’ve made yourself accessible and available to your team, change is scary, and they might still have unspoken questions or fears. Leaders especially aren’t always privy to side conversations or what team morale looks like on the front lines. In order to successfully navigate change, you must understand how your people are actually responding. Find your champions—the people who will tell it like it is—so you can take action and address the needs of your team. Even if those people don’t report directly to you, make time to connect with them. 

“I don't get the hot tea anymore. I wish I did. I try with my skip-level meetings on Fridays, but I can't get everything out of them. And so I think creating ways to get that feedback is so important.” – Shay Keeler

5. Create a safe place to fail

Failure feels scary when a lot is on the line. Particularly after a major organizational shift, people need to know they’re in a safe environment to make mistakes. It’s likely you’ll be evolving your processes, coaching strategy, messaging, and sales scripts alongside those transitions, and let’s face it: we don’t always get it right the first time. Use failures as opportunities to coach on a deeper level, better understand your audience, and optimize your processes. This is a great time to lean on your enablement and marketing partners to figure out what works and what doesn’t. 

“In order to create a culture of winning when you're going through disruption, you first have to create a culture of losing. Your priority number one is to get people to try. It's not to get people to win at it or be good at it. It's just to get them to try.” – Jen Allen

Watch the On-Demand Recording

Change is the only constant—but when we prioritize our sales cultures, we’re better equipped to navigate whatever lies ahead. Watch the on-demand recording of my conversation with Jen and Shay for more insights and tips on creating a win-win sales culture here.