Strong leadership has always been, and will always be, an undeniable need for any sales organization to be successful. So much so that you should make a concerted effort to confirm that trusted, experienced sales leaders are in place on any new sales team you’re thinking of joining. But one area of leadership, especially in sales, that I’ve found equally important, and perhaps a little less discussed, is that around leadership development.
Every sales manager, director, or VP wants their team to do well, hit their quotas, and join them at President’s Club each year, but how much are they doing to increase the likelihood that those things happen? In many cases, young sales professionals are required to “drink from the firehose” of on-demand courses to ramp up on learning a new product line, then it’s practice-pitching-sessions, CRM tool access is granted, marketing comes in with endless wiki pages full of decks, case studies, and battlecards, and you’re off.
Congratulations, you are officially…enabled. But, enabled to what, exactly? Sell? Sure. And don’t get me wrong, you need to be enabled to sell.
But are you enabled to one day lead? Not exactly, and this is where many high-growth software companies fall down or miss the mark. To be fair, none of what I laid out above is intended to enable you to lead. There isn’t a learning platform or tool on the market that was built to enable strong, future leadership.
That responsibility sits squarely on the shoulders of your sales leadership team. They should be held accountable for it, and their managers need to support the time investment that needs to be put into building a holistic leadership development program.
Here are three key components to a robust leadership development program that I’ve seen firsthand result in a valuable ROI.
Understand what “winning together” really means
One of the most common misconceptions about “winning together” is to equate it to merely celebrating together or being rewarded together. If a company hits its annual revenue target, thanks to a small handful of large deals closed by a small handful of account executives, there will likely be (and should be) some celebrating that’s done together and, ideally, not just within sales, but across the entire company. Likewise, the entire company may then be rewarded together, maybe in the form of a bonus, a splashier holiday party, or nicer swag – rewards come in all shapes, sizes, and monetary amounts.
So, what’s winning together, then? Winning together means just that. It’s cross-functional teams leaning into the roles they each play in helping customer-facing teams win more customers. As leaders, it’s our obligation to enable our teams to win, to mentor our teams to win and to foster a winning culture that recognizes every win.
Lastly, every win means every win – not just those that happen here in sales. In many organizations, closed deals often include valuable contributions from marketing, finance, legal, and engineering or the product team – do they receive due credit for those wins? What can you do to make sure that happens?
And, while winning cultures likely vary from org to org, there’s one requirement they all share.
Celebrate wins of all sizes
In a fast-paced tech company, it can be very easy to lose sight of taking the time to recognize individuals for their hard work and accomplishments. However, it’s vital to understand how important it is to not let this happen. Everyone on your team needs to feel seen, respected, and rooted for. This is true whether you’ve been with a company for years or even if you’re in your first few months. Great work should be recognized and celebrated, and celebrated often. The best leaders are able to spot these opportunities by spending the time it takes to fully understand the work that went into each win. This requires being 100% focused on bringing business value to every individual, company, and your team, every day.
To make sure every win – no matter how “small” – is celebrated, think about not only shining a light on those smaller, individual contributions but giving those individuals the opportunity to shine a light on themselves. Maybe they can share that win at your next standup meeting, maybe there’s an available segment in the next internal newsletter or even an upcoming all-company meeting.
Bringing increased visibility to contributions large and small shouldn’t feel like a burden, not when you know the increased morale, motivation, and retention these efforts bring.
A responsibility to inspire
This really is the fundamental principle of winning together that I try to drive home with my own leadership team. Of course, we need to educate, and enable, and “arm” our teams. But we also share a responsibility to go further. We have a responsibility to inspire our teams not to simply “do their jobs” but to bring their best selves to work and just as importantly, if not more so, to our customers each and every day.
There’s so much expected of leaders, no matter what level of leadership you’re talking about. But if you wake up each day with the goal of inspiring your teams to be their best selves, and you’re successful at doing that, it’s going to put your company in the best position to continue to grow, reach your goal, and break records.
There’s another point to winning together, and that’s to also avoid anyone feeling like they’re “losing alone.” Losses are going to happen. That’s just the nature of sales. Some organizations take losses hard but fail to capitalize on all that can be learned from them. High-performing organizations aren’t afraid to lose; they recognize the opportunity to improve, and they know they’ll be in a better position tomorrow.
There should be no shame in losing. Not when you’ve built a culture that leaves so much more winning together that’s left to be done.
