Back in pre-COVID times, one of my favorite activities as a leader was to get out on the road with a member of my team and join them for a big onsite pitch. I’ve never wanted to turn into a spreadsheet jockey manager who spends his days analyzing reports and shuffling schedules, so I made it a point to head into the field at least once a month (and sometimes more) in order to understand the reality on the ground, and get the opportunity to provide hands-on coaching and add value in big deals.
In order to make the most of my time away from the office, I came up with the following game plan for every trip into the field.
Align on Outcome
Once the onsite has been scheduled and I’ve decided to join, I’ll always insist on an alignment meeting with my SC and the AE. If we’re going to spend corporate resources (time & money) on making the trip, I want to make sure that we have everything we need to drive a successful outcome.
Establish the Win Plan
I like to discuss everything from attendees on both sides, meeting format and agenda, establish roles for each person on our side, define risk factors, and most importantly, win themes.
Finally, depending on the amount of time we have until the onsite, I’ll push for a basic project plan so that everyone is aligned on what we need to do to prepare in advance in order to successfully execute and hit our meeting outcomes.
Be a Prepper
With the initial prep meeting out of the way, now it’s time to dive in and do the heavy lifting of getting ready for the meeting. The level of effort required here has varied at each company I’ve been at - everything from basic demo customization to building out a full
demo environment mapped to the prospect’s branding and configuration requirements. When I was an individual contributor, I would generally block off a Friday the week before the onsite and hole up at home to do the work, and finish up anything lingering over the weekend so that I could hit the ground running the following week without having any additional work hanging over me.
Divide & Conquer
I’m not a procrastinator and hate last minute all-nighters, so I try to gently infuse this same spirit of planning into my team members by taking a divide and conquer approach with the prep work. I do this for two reasons - first, it helps free up some capacity for them to support other deals, and second, my hope is that it demonstrates that I’m willing to help on any task, no matter how small, in order to ensure we’re successful.
And finally, by taking this approach, it avoids a last minute scramble and all-nighter the night before the meeting. As I always like to say, if the company is going to spend thousands of dollars to go pitch a big customer, the last thing we should be doing is showing up for the meeting running on fumes, exhausted and haggard. Fresh, rested and prepared wins the day every time.
Establish an Active Role
I like to establish what my role will be in the meeting. I’m not a fan of showing up without a role, and just sitting there taking notes like a bump on the log, or even worse, trying to inject myself into the meeting to show I’m providing value and am the smartest guy in the room. Both of these scenarios just makes us look disorganized, which lays a seed of doubt in the buyer’s mind around whether we have our shit together as an organization.
In terms of the roles I’ve typically played, it runs the gamut. In some cases I’ll be there primarily to build relationships at the executive level in the room. In other cases it’s more hands on - everything from being an active listener and asking second and third level discovery questions that are often easily forgotten when you’re on the hot seat as the presenter, to being back-up tech support or even being on Slack to quickly “phone a friend” in Product or Engineering if something goes off the rails.
No Mister Boss Man
My preference is to never introduce myself as the manager/boss of my team member. I want the customer thinking that my team member is the expert, and not turn to me to validate answers he or she is providing. I’ll play around with titles depending on the audience, and usually go for something like Platform Architect, Solutions Evangelist, Director of Customer Solutions, or something else that sounds slightly made up. But what you’ll never hear me say is “Hi, I’m the boss/manager of your SE/SC.”
Add Incremental Value
I view my role in the meeting as being there to add incremental value on top of what the AE and SE/SC are providing. My role isn’t to be the guy who repeats everything they say, talks over them to make a key point, or anything else that is a distraction to the agenda of the meeting. What I mean by adding incremental value includes discussing a customer story to illustrate the value of something we just covered in the demo, covering a particular part of the agenda if it aligns with an area of my expertise (I usually pick integrations and governance, because discussions around these topics are often quite nuanced), and general blocking and tackling - things like creating a parking lot for questions to cover at the end of the meeting, asking the customer to explain their use case in greater detail to buy my team member some additional time, or creating a list of follow-up actions for after the meeting.
Take Minimal Notes
Speaking of creating lists or taking notes, I try to keep this to a minimum. I remember early in my PreSales career being thrown off my game more than once by a manager who took copious notes during the meeting and then proceeded to tell me everything I did wrong five minutes after the meeting ended. While I didn’t notice his note taking the first time, rest assured I did every time after that and it planted the seed in my head that I was somehow doing something wrong. I made a promise to myself that when I got to the point where I was leading people, I would keep my note taking to a minimum and not provide immediate feedback after leaving the meeting (unless asked for it explicitly).
Hit Pause on the Debrief
I’m sure some leaders will disagree with me on this point, but I prefer to wait until the next day to provide feedback and coaching. My exception to this rule is if my team member asks me for feedback right away, and even then I’ll ask if they’re absolutely sure. My rationale on doing this is quite simple. After a multi-hour meeting book-ended by travel, nerves are frayed and everyone just needs a break. If someone crushed the meeting, then by all means I’m going to let them know for positive reinforcement, but if there are critical areas of feedback to deliver, I’ll wait until the next day. I’ve found that not only is the person on the
receiving end more receptive, but chances are good that they’ve thought through what they could do to improve, and will come to the table with actionable follow-up steps to take. I love this type of self-awareness and accountability, and prefer it to nitpicking on something five minutes after the meeting ended when that person is more likely to get defensive. And along these lines, I’m a firm believer in the concept that there are many right ways to say or do something. I’ve seen all too many managers who view “coaching” as telling their team member how to do it their way, versus finding the way that works best for that person. While this might work in the short run, especially if the person receiving the feedback is struggling, I’ve found that it does little to address the underlying issues and misses an opportunity to help the person find their own path, and build confidence in their abilities along the way. More on this in another post down the road.
Provide Ongoing Support
Once the big meeting is over and we’re back at home, I try to make it a point to stay involved in the deal and provide ongoing support. While this doesn’t always come to fruition - sometimes we win or lose quickly, or I get pulled in another direction - I’ve found that being intentional about striving for ongoing support and involvement on a deal generally means it will happen in some form or fashion. I do this not to be a micromanager, and I have supreme confidence that each of my team members are highly capable and can support the deal on their own. I do it to better understand what’s working and not working, and to have empathy and understanding for everything that my team faces. It’s really easy to create Powerpoint decks illustrating a new process or workflow, but seeing how it holds up to reality is very illuminating and ultimately results in better processes and work streams for all involved. As Mike Tyson once said, “Everybody has a plan until they get punched in the mouth”. Staying involved in the deal is my way of getting punched in the mouth. It keeps me honest and allows me to truly support the needs of my team.
Final Thoughts - Find Some Joy
Last but not least, I think it’s very important to find some joy when traveling for work. Finding joy means different things to different people. For some it’s checking out a great restaurant, for others it’s going for a long run or enjoying some peace and quiet in a hotel room with room service. Let’s face it - business travel can be a grind (stay tuned for another blog post on this topic). Between time away from your family, early wake-up calls and interrupted sleep, delayed or cancelled flights, hotels and motels that could be Anywhere USA, and sometimes suboptimal dining choices, life on the road can be challenging at times. And will probably become even more challenging in the near future as we all deal with COVID considerations.
So when I join a member of my team on the road, I make it a point to be considerate and not up in their grill 24/7, and find ways throughout the journey to connect with them as another human being. This starts at the airport. I’m fortunate to have lounge access, so I always make it a point to extend the invitation to my team member, but I also make it clear that the invite is not mandatory, and that if they just want to zone out at the gate at 5:00am, I’m totally cool with that. On the flight, I’ll make sure we’re not sitting together, because let’s face it, no one wants to sit next to their boss on a 3-4 hour flight at six in the morning.
Once we’re at the destination, if the meeting isn’t until the next day, I always try to find a nice restaurant for us to eat at that night after doing any final prep work. If we’re staying out in the burbs near a corporate headquarters, I’ve been known to pay for Uber out of pocket
and head into the city in order to eat somewhere fun that I research via Eater or Bon Appetit; life is too short for chain restaurants. While at dinner, I’ll make it a point not to discuss work and focus the conversation on making a personal connection. I love learning about people, so hearing about another person’s family, their hobbies, their personal aspirations, or even just sharing funny stories, is much better than talking shop and turning into corporate drones.
Following the meeting, there’s nothing better than that ride back to the airport, savoring a job well done, and relishing the thought of sleeping in your own bed. Once through security, I’ll suggest a celebratory beer if there’s time before boarding, and focus the conversation on all of the great things that we did (the constructive feedback can wait until the next day).
And then finally, if all goes as planned, home sweet home. Enterprise sales can be a grind at times, but the hard work is well worth the effort, especially when it involves building relationships with other people.
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.