If you’ve known me longer than five minutes, you’ll know that I place a heavy emphasis on the value of a collaborative and cohesive team that is high performing, and provides a safe space for each member of the team to be themselves, speak their mind, and grow in their career. And most importantly, have fun while doing it. In today’s world with fully remote, distributed teams and uncertainty about what the future holds, this is more important than ever.
While I don’t pretend to have all of the answers on how to build and nurture a high performance team with these attributes, I do have some thoughts and ideas that I’d like to share around what has worked for me. As I’ve grown in my career as a leader, I’ve viewed my approach as my “special sauce” and part of what makes me unique. I’m fully cognizant that this approach is one of many out there, but it’s worked well for me and fits my style. And the proof is in the pudding -- the teams I’ve managed have had consistently low attrition, high levels of engagement, and colleagues who have joined me across multiple companies. So with that, let’s get started!
Set the Foundation
Having a team charter in place is a critical component to defining what role the PreSales team holds within the organization. Is it 100% focused on PreSales, or does it cross the line into post-sales support in some form or fashion? I’ve seen all kinds of versions of what PreSales teams are responsible for, and it’s easy to take on more than you signed up for, so putting it on paper is key to informing the rest of the organization on what your team is focused on doing. For the team charters that I’ve put together in each of my three leadership roles, I start by breaking the charter into External and Internal statements - i.e. how do I describe the team to a customer versus a colleague.
On the next set of slides, I list out the team’s focus areas into two buckets - primary and secondary. Primary focus areas are the activities we focus on to support deals, and secondary focus areas are the activities we focus on to support collaboration with other teams. I’ll then have a set of slides that describe the team’s engagement model - i.e. how, when, and why Sales should engage with us to support deals. Finally, I’ll have a set of slides that walk through the team’s operating pillars - i.e. what are we doing from an operational standpoint to support our charter and build towards being a world-class team. And to top it all off, I’ll create different versions of this charter deck to use for different audiences.
Lead by Example
This one takes on a variety of meanings for me. At the most simple level, I lead by example in how I choose to operate on a daily basis. I show up to meetings on time. I’m focused and present when I’m in those meetings. I don’t waste time in meetings and try to end them early. I treat every colleague with respect, regardless of how they act or what level they’re at in the organization. I write thoughtful emails that aren’t ridden with misspellings and grammatical errors. It also means I’m willing to get in the trenches with my team and do whatever it takes to get the job done, or in some cases help get the job done on lower value activities (RFPs, Infosec questionnaires) in order to free up a team member’s time for higher value activities (more on this one later).
Additionally, I do my best to lead by example when it comes to living a balanced life. I don’t send emails at 11pm at night. If I work on the weekend, I don’t email or Slack people, or advertise it on Monday morning to make people feel bad. I take vacations and disconnect. I don’t pretend that I have all of the answers, or have a “my way or the highway” approach to the role. And most importantly, I’m not the “Super SE” who zooms in to show off on big deals, and takes the limelight from my team.
Celebrate Core Values
What I mean by this is intentionally celebrate the activities and behaviors that are part of the team’s core values. For the teams I lead, I place a heavy emphasis on teamwork and collaboration. While I’ll be the first person to celebrate a big win where a member of my team played a key role, I’m equally likely to celebrate when someone on the team goes above and beyond on a project that benefits the entire team. Or when someone pitches in to help a teammate on prepping for a demo, or answering questions on a complex technical concept. The quiet little things that happen behind the scenes are what lifts the entire team’s knowledge over time and allow us to scale and operate more efficiently, so you bet I’m going to emphasize and reward this.
Team Projects & Initiatives
I’m a big fan of finding projects that the team can work on as a whole, in smaller pods, or as individuals. I don’t believe in creating work just to stay busy, so I always look at each project or initiative through the lens of “will this make us better as a team?” If the answer to this question is yes, then I’ll work with the project owners to define a scope and timeline for completion. Speaking of timelines, while I’m all about operating with urgency in sales cycles, unless the project is dealing with a critical gap that needs to be filled immediately, I’ll usually set very realistic deadlines. I’d much rather have a well-baked outcome than something that the team rushes through in order to meet an arbitrary completion date.
Deliverables that Scale
Anytime someone on my team creates an awesome deliverable - whether it be a piece of collateral, a deck, a short demo snippet, or anything else for that matter - they’ll inevitably hear from me something along the lines of “Hey, that looks great! You should templatize this so the rest of the team can benefit.” I’m a big fan of creating repeatability in sales cycles in terms of how we support deals, and deliverables that have a positive impact on moving sales cycles forward are always at the top of my list to replicate. By always looking at the great stuff that my team is creating through this lens, and then constantly reinforcing the need to templatize, over time it builds a new habit in the team and thus another operational muscle.
Share Success Stories
In my current team, we now have two weekly meetings, each with a specific agenda. While our Monday morning meeting is focused on team housekeeping items and sales process, our Thursday morning meeting is primarily focused on learning, and a big part of that is sharing success stories out in the field. Sharing these stories accomplishes two goals in my mind. First, it serves as a great learning opportunity for the rest of the team. If someone has developed a strong talk track that resonates, or has an effective way of overcoming a common objection, I want to create an environment where the rest of the team learns and benefits from it as well by putting into action.
Second, it provides an avenue for individual team members to showcase the great work that they’re doing out in the field in a way that provides benefit back to their peers. I was on a team many years ago where everyone held back these golden nuggets to create competitive advantages for themselves. This always felt counterintuitive in my mind, when instead it could have been used to create a competitive advantage for the entire team, and as a byproduct, the sales team and company as a whole.
Seek Feedback… and Act On It
I recently sent out a “Team Focus Survey” with the intent of gathering anonymized feedback from my team. And boy am I glad that I did! The survey data that came back was detailed, nuanced, and full of actionable insights that I’ve immediately begun putting into action. While I certainly could have sought this feedback through other avenues, including 1:1s and team meetings, I’ve found that when people are put on the spot, the feedback you’ll get back is different than when they’re given the opportunity to spend time thinking about it and writing thoughtful responses. Although this is the first time I’ve run such a survey, it definitely won’t be the last. And more importantly, the survey results will go a long way in helping make us a stronger team by giving everyone input into how we operate.
Create a Safe Place
Private Slack Channel
This one might seem like a no-brainer and I suspect most teams already have this, but it’s still worth mentioning. Having a private Slack channel for the team to collaborate, problem solve, vent, and just be silly from time to time is a great way for distributed teams to stay connected and build camaraderie. What about a public PreSales channel, you ask? In my experience, there are several ways to solve this. If you’re operating in a direct assign model, this may not be necessary since most AEs will go directly to their assigned SE for support. If you’re operating under a pooled model, having a public channel might be a good option as long as there are reasonable SLAs in place during and after business hours, and also an expectation that the entire team will participate in assisting with questions.
Another iteration of this is a “Sales Support” channel that includes a variety of cross-functional participants, including PreSales, Support, Product, PS, and Customer Success. While PreSales will still end up fielding the bulk of the questions, it gives other teams a chance to flex their knowledge muscle and feel more bought into the common mission of driving revenue growth.
It’s OK to Vent
As a leader, I have no problem when someone decides to vent about a frustrating situation, either directly to me or other team members, or even in a team meeting. Life is messy, and we’re not automatons. What I’ll say here is that I would prefer someone venting in a forum where I know about it, versus squashing it and pretending like it doesn’t happen. By having visibility into frustrating situations, it provides me with leading indicators on small problems that may eventually become bigger problems, and it allows me to begin planning ahead to solve the issue proactively.
Problems = Solutions
Speaking of venting, my preferred method for someone venting or complaining about something is to get it out of their system, and then channel that energy towards developing a solution. While this isn’t a unique approach, by making it a key part of our team culture, I believe that it encourages people to speak their mind about frustrating processes or systems, and then redirect that passion to work on a better approach. I have numerous examples of where I’ve seen this turn into huge success stories over the last few years, and as a result, I’ve made it a core part of how I operate.
Keep it Real
Don’t be so Serious
Life these days is pretty serious. Between a global pandemic, an economy on the edge, and various other current events I won’t delve into, things are about as real as they get these days. And while the business of enterprise SaaS is serious in the sense that we’re solving complex problems for our customers and helping create value for our investors, it doesn’t mean that everything has to be serious all of the time. While I’m pretty buttoned up around how I operate and manage my teams, I also infuse that with a healthy dose of fun and humor, and not just in the form of structured events or activities (although team bonding outings are definitely fun and I miss them right now).
What I mean by this is give people the room to do their job, and do it in a way that best fits their style and strengths. While I maintain a weekly cadence of 1:1s with every team member and join strategic opportunities for support and coaching, I avoid getting into conversations around how someone is spending their time unless there are major performance issues, or if they proactively come to me asking for advice on time management. As a former individual contributor, it can be very tempting to play the “let me tell you how I did it” game, which having been on the receiving end of that conversation, I can tell you can be extremely demotivating.
And while I’m on the subject of providing advice, before I embark on any coaching journey, I first seek to understand a team member’s style and their strengths. While I’m aware of what their weaknesses might be, I’m less concerned about those early on. Once I have that baseline in place, the coaching and guidance I provide is always through the lens of amplifying strengths and turning weaknesses into opportunities for growth.
Provide Air Cover
There are two ways that I view “providing air cover.” The first, more traditional version is what any good leader does. They provide air cover for their team in challenge situations, internal politics, and supporting them when asked. The second, less traditional version is providing air cover on deals when there’s a confluence of events that are extremely bad timing. Here’s what I mean by this. Let’s say that it’s Monday and an SE has a big presentation they’re preparing for on Wednesday morning, and they have all of Tuesday blocked off for prep and dry runs. And lo and behold, at 5pm on Monday, a last minute Infosec questionnaire comes in on a deal that is scheduled to close on Friday, and it’s due Wednesday at 12pm (the same time as the presentation).
Rather than telling my SE to just “suck it up and work late both nights,” I’ll proactively jump in and take the questionnaire of their plate. Sure, this will potentially take away from other things I could be focused on, but if someone is going to work until midnight on Tuesday to get the questionnaire finished, I’d rather it be me than the SE who has a big presentation on Wednesday morning. I view the presentation as a high value activity that can have a big impact, whereas the Infosec questionnaire is a low value activity (sorry Infosec folks!) required as a checkpoint for a deal closing. I’m sure this approach is a bit controversial, especially for Director/VP level leaders in bigger organizations who have the luxury of bountiful resources, but as a first-line leader in a fast-growth start-up, I view it as table stakes and an easy way for me to add value back to my team members. And you can bet that I’m tracking these deliverables and the time I spend on them in an effort to make a case to the business to add more headcount on the Security team!
The Sum is Greater than its Parts
In closing, I recognize that many of the things I’ve described here are pretty common across leaders regardless of function, but when they’re added all up and become an integral part of a team’s operating model, I’ve found that the results and outcomes always exceed the efforts. And just as a teacher would be proud to have a former student reflect years later on being the “best teacher I’ve ever had,” I believe it is a worthy goal to have the same thing said about being the best leader someone ever had.
Chris is a highly accomplished PreSales leader with 15 years of experience building, scaling, and leading teams in competitive enterprise SaaS markets. He is currently Director of Solutions Consulting at Dynamic Signal.
Connect with Chris on LinkedIn.