Five Ways To Earn Trust As a Sales Leader

Being a VP of Sales in the world of SaaS is tough. By many accounts, the average tenure for someone in this position is only 17 or 18 months. What’s more is that this figure has seemed to be fairly consistent over the last decade. Suffice it to say, whatever is making it challenging for a VP of Sales in the software world to be successful has not really been addressed.

To be sure, there are external factors that likely contribute to the short tenure of a sales leader. For one thing, most software startups fail. It is not easy to build something from scratch. There is also not one-size-fits-all winning formula for every company. As a result, some companies hire much too soon or much too late. Others grow at all costs while ignoring product or operational deficits which come back to bite them later. In yet other cases, a Founder may be beholden to their investors in a way that precludes them from leveraging their own experience to the fullest. While it is unfortunate that the sales leader seems to bear the brunt in disproportionate fashion, the reality is that in many of the aforementioned circumstances, the company is unlikely to be successful irrespective of who is in charge of revenue generation.

With all of this in mind, it is important for sales professionals to bear in mind the factors that do reside within their proverbial locus of control. One basic truth about sales leadership is that no leader can be successful without a great team that is bought-in to the mission at hand. Simply hiring great people is not enough. Great sales leaders get the best out of their people through good times and bad. In even the most successful software companies, there will be both ups and downs, so it is vital to gain long standing commitment from the team to maintain its focus at all times. The key way to get buy-in? Earn trust. With that being said, let’s look at five simple ways to earn trust as a sales leader.

1. Advocate for your team

There are two ways to advocate for your team: with leadership, and cross-functionally.

With leadership, the advocacy for the team also comes in multiple forms. One way it comes up is with resourcing. An effective sales leader comes into the organization with a clear understanding of what resources can be made available to the team. For example, when hiring Account Executives (AEs), it might be important to also understand whether or not there is headcount for Sales Development Representatives (SDRs) who can partner with the AEs to help fill their pipeline with quality leads. Another important factor would be what software tools are made available to the team to help them succeed. On yet another level, it could come down the compensation for the team, their territories, or how their quotas are set.

Cross-functionally, a good leader also needs to ensure that the sales team is set up to do its job as effectively as possible. This means that if there are glaring product deficits, the sales leader is gathering that data and building a compelling internal case to the leadership team (including the product leader) as to what enhancements need to be made. I once worked in an organization a long time ago where so much of the work was manual across all of the teams that the salespeople often found themselves doing work that probably should have been within the Customer Success or Operations teams. This non revenue generating activity frustrated the salespeople and made their jobs more complex. 

2. Lead from the front

Another good way to earn the trust of the team is to lead from the front. One of my favorite images of leadership is twofold. On one hand, a leader sits from his chair and tells his people to move a big rock. In the other image, the leader just moves the rock for the team. Good leaders move the rock. Bad leaders tell people what to do.

Your job as a leader is to help people succeed. The best way to help people succeed is to go out and do the hard things that they do not want to do themselves. This includes some of what I already mentioned – sitting in all of the internal leadership meetings and advocating for the team. But leading from the front can also be a lot more menial. When you are telling your team that they need to spend a lot of their time writing cold emails or making cold calls – which is usually not considered to be a “fun” activity – the team is a lot more motivated to do it when they see you doing it too. This is why whenever I organize a day for cold outreach that I participate in it myself and get competitive about seeing whether or not anyone will beat me. When salespeople get a few extra at-bats here and there because you pinged someone in your network for them, it goes a long way towards them respecting you.

Do the hard things. You will not regret it.

3. Explain the why

Sales process is very important. It helps everyone to speak a common language and if implemented properly, it optimizes the odds of success across the team. It also provides the team with structure that they know how to follow and makes coaching much simpler and more objective.

That being said, buying into a process is pretty challenging if you are not aligned to why the process works. One of the easiest ways for dysfunction to come about is when members of a team feel like they are being told to do something while not agreeing with it. This is when people start gossipping with one another about all the existential issues that must be fixed. The moment you lose the “Why,” you lose the team.

A lot of leaders believe it is not important for their team to understand why certain decisions are being made. “That’s for leadership” they tell themselves, as if having a specific title makes them privy to basic information that others cannot have. To be sure, of course there are sensitive topics only leaders have access to. But changes in strategy is not one of them. When you are experimenting with something new – even if it is due to a deficit in the forecast – be honest about what you are doing and why. The precise moment that the team feels you are being dishonest with them is the exact moment you lose their trust and by extension, their buy-in.

4. Know their why

Something I like to do in the first days with a new team is an exercise about understanding each other’s “Why.” The reality is, no one came out of the womb to go work at someone else’s tech company and to enrich a founder or co-founders that they hardly know. Nothing wrong with that, it’s just human nature that everyone is intrinsically motivated for some other reason, and their job or career is generally a stepping stone towards achieving whatever that is.

The thing about the “why” is that it is rarely – if ever – the first thing that comes to someone’s mind. Let’s face it: most salespeople worth their salt will tell you that they want to make a lot of money. And while at face value it may seem that these salespeople are greedy, if you ask them “why” over and over again, you will usually find that they want to earn money in order to do something else. It might be to travel the world. It might be to provide for their family. In my case, it was to give back to others. When I had a daughter, my “why” changed to her, but of course giving back to others is still very important to me.

So, why is the “why” so important for a team? 

Two reasons.

For a leader, it is important to know what makes everyone tick. It is a lot easier to speak to someone through the lens of their real motivation rather than through the lens of pressure they may feel at work. In that context, the conversation feels more personal and authentic, and is therefore much more likely to create trust and buy-in. Moreover, when the team shares their respective motivations with one another, it fosters deeper understanding for team members of one another.

Imagine a scenario after this exercise where one team member feels a bit like mailing it in today. Is it not much harder to do that now that they understand that one of their teammates is trying to pay off student loans, or that another moved a dozen times as a child and wants to provide a stable environment for their children?

5. Be vulnerable

Based on the last method to earn trust as a sales leader, the last one should seem fairly obvious. When you are vulnerable with your team, you are authentic. I define authenticity as “presenting an honest version of oneself.” Being authentic does not mean people like you. It just means that people believe what you say.

Look, no one can relate to someone who is perfect. And the simple rationale for that is that nobody is perfect. Leaders who never admit their mistakes are frustrating people to work for. Leaders who hold themselves accountable and admit their mistakes are perceived as intellectually honest people. This means that whenever they roll out new ideas or give feedback, the team knows inherently that the leader will be fair-minded about the outcome.

One of the best ways I like to give feedback to team members is by speaking about experiences where I made a similar mistake. When I give feedback this way, it shows them that I am just like them and susceptible to the same shortcoming in my thought process. This makes the feedback a lot more genuine and impactful. We all tend to laugh at the person who makes fun of themself. But we also root for that person a lot more than the person who brags about their achievements all the time. The more we act like the vulnerable person interested in getting better, the more we relate to the team because they are very much the same way in their earnest effort to win.