Leadership and Management
February 26, 2024

Leadership is So Much More than People Management


Cassie Young

In the business world, it’s common to conflate leadership with people management, but they are two very different things. While people management is a great path for some individuals when the time is right, it is not the only way to showcase leadership, and it’s certainly not for everyone. I recall an article I read a few years ago that said something along the lines of, 10% of the population are natural-born people managers, another 20% can be coached into being great managers, and the other 70% should never manage people! The challenge is that people often feel as though they must manage a team to be important, which couldn’t be further from the truth. You absolutely do not have to be a people manager to have a tremendous business impact; in fact, many of the highest-impact people in my organization are individual contributors who do not manage people! Leadership can and should be exerted in many ways beyond how many nodes you have on the org chart. Reflecting back on my time as a high-impact individual contributor, as well as my years, managing large teams, I have several recommendations for how to exert leadership:

1) Trust your gut, but also use data to guide your decisions.

My most formative moments as a leader have come when I’ve used data to make tough decisions.Once upon a time at Sailthru, we were significantly invested in traditional sales methods like SDRs and outbound prospecting. That said, when we talked with our customers, they told us that is simply not how they buy; they asserted that they look to their networks/people they trust for these decisions. Our numbers supported that much: we saw ~80% of our pipeline coming from some type of referral, and those opportunities had double the close rates of traditional channels.With this data in-hand, one hundred days into my current role at Sailthru, I had to make a very tough call to cut our commercial team by about 65%, something that we’d never done before as a business, to shift those funds into higher ROI channels (i.e. investing in customer success is a flywheel for referrals). Six months later, our SaaS metrics were up and we were landing some of the most exciting logos we’ve ever signed.The highest-impact business decisions you’ll make are often some of the hardest ones you’ll make, but such is leadership. I always tell my team to trust their gut on instinct, but then leverage an analytical framework to back it up with data.

2) Challenge the way things are done.

True leaders are always looking for opportunities to shake up the status quo in order to make an impact. To cite some specific examples: the best sales reps we have are not just the people who close the largest deals, but rather those that constantly evolve the way we sell, thus setting a new model for others to follow. Our strongest CSMs are the individuals who chart new paths around how to drive value for the customers and then enable/teach their peers to do the same. Leadership often happens through influence versus just through direct line management.(Going back to #1, even better when you can measure the impact of the changes you are making! For instance, at Sailthru we know that customers who receive a certain type of strategic business review boast an NPS significantly higher than those who did not.)

3) Learn from your customers.

Be maniacally obsessed with your customers. I make it a point to meet with at least one customer every day, if not more, which sets a pace and expectation for the rest of the team (for a different day - leading by example!). When I meet with customers, they elevate my industry knowledge and advance my strategic perspective, which prompts me to think about new products or services we can provide. This can happen at every level; I recall our training team recently changing what was deemed to be a high-impact training program after leaning in on customer needs, only to roll out an even higher impact program. In SaaS businesses, if you are looking for places to make a tremendous impact, your customers are almost always the best place to start.

4) Over-communicate with your team.

It’s been said that people need to hear something seven times before it sticks, and my experience has demonstrated that this is very much true! Communication is instrumental across every level of an organization, regardless of whether you are communicating “up” or “down.” I implore managers to over-communicate with their teams, and try to set an example for them; for instance, every Monday night I send around a weekly digest with detailed updates on how we’re doing commercially as well as cross-functional happenings around the business - just in case teams forget to talk to one another! For individual contributors and managers alike, there is arguably nothing more important than “managing up” and avoiding surprises.

5) Provide feedback as close to real-time as possible.

Feedback is most effective when it happens in real-time (or as close to it as possible). When you fail to give feedback in the moment, the feedback inevitably becomes less specific (i.e. “it feels like you aren’t paying attention in meetings” vs. “in that meeting just now I noticed you buried in your laptop the entire time and it appeared as though you weren’t paying attention”), and is thus significantly less useful or impactful to the recipient. This is something that is very hard to remember to do - I still have to remind myself about this on a daily basis - but is critical. As a manager, you should also go out of your way to seek feedback from your team; if you are uncomfortable doing so, ask your People team to assist you either by running formal or informal 360 reviews, conducting an engagement study, etc. In the ideal state, performance reviews should be incredibly anti-climactic because feedback is continually provided.

6) Hire people smarter than you to make your business stronger.

As a leader, there are going to be countless times in your career where you think, “do I actually have the skills to do this job?” Guess what - as the leader, you need to figure out how to make it happen! This means making the right hiring decisions to ensure you have the people who can execute well, especially in pockets of the business where you yourself are less confident. My dad always used to say, “you’re only as strong as the team that supports you,” and I couldn’t agree more. When I first arrived at Sailthru, I was primarily focused on customer strategy, data analysis, and general management. When it began apparent to me that our support team had opportunities for improvement (again, see #1!) and I brought those insights to our CEO, he handed me the keys to the support team - a function I knew nothing about! My first move was to hire the absolute best support leader I could find, someone who could do that job 10x better than I ever could. His leadership made the team stronger as well as my own leadership stronger. I’ve since done the same in multiple functions at Sailthru, and it has paid dividends in terms of the resulting business impact. The other important dimension here is to ensure your team continues to be the best possible team; a mentor of mine once told me that “just because your team won the World Series three years ago, doesn’t mean you make the team today.” As a leader, it is critical you are always matching your talent to the needs of the business in the present state.