A random text from a friend lit up my phone asking if we could do some network design work in the Caribbean. You can’t make this stuff up.
We’ve been in a bit of a sales desert for the last 40 days, with me personally leaning in as hard as I can to our new “Raving Fan Factory” ethos. I’d been on vacation in Ireland for ten of those days, and it never fails to amaze me. I can sit at my desk in Richmond for weeks on end with zero customer communications, then the second I leave town a bat signal gets thrown up in the sky alerting the world that now is a great time to throw some curveballs my way. I’m not complaining, but the pattern is undeniable. I guess the old saying “if you’re bored, pack your bags” rings true.
I asked my friend to make the introduction over email and told him I would take it from there. A few minutes later the message popped into my inbox. The prospect was helping a family member with a large sugar plantation, and it was clear they were already down the rabbit hole with a partially baked Wi-Fi installation. My turducken alarm started going off. He wanted to know which piece of mesh gear he should buy to round out the install.
Also by Henry Clifford: What Would You Do for a Raving Fan?
I’ve seen this movie before. Doing exactly what we’re asked in this situation leads to a frustrated client down the road. I also shuddered at the thought of one of our junior salespeople fielding the same query. Our industry has a vein of people-pleasing “Mother Teresa” energy that can lead us astray during initial research. Rather than push back or ask questions until we’re satisfied, we veer too easily into client-driven solution design. They didn’t call us because they wanted to design the system. They called us because they’re in pain and we have the medication. So why do so many of us cave to prospect demands knowing the end-product might go sideways?
Honestly, I initially felt like a failure with this interaction. Was it because I haven’t fully replaced my own ability to handle edge case inquiries? Maybe it was because we don’t have a deep bench trained to fact find properly before designing solutions. Either way, it got me thinking about training and selection. People pleasing is a great trait to have in an employee, but those same quirks can run a project into a ditch if they go unchecked. Here are a few antidotes we use to help our well-meaning junior reps engage with strong personalities without getting steamrolled.
- Don’t go it alone. Senior salespeople should bring a junior along for mentoring and to streamline their own time. A good seasoned rep leverages a junior to take notes, send recaps, and handle the admin side of meetings so proposal handoffs and next meetings actually get scheduled.
- Avatar selling. Match personality types together. We’ve always tried to round out our sales team with representatives from our customer cohorts. People like to buy from folks they’re comfortable with
- Ask “Why?” Give your salespeople explicit permission to ask questions until they’re satisfied with the outcome. Tell them you’ll have their back if they get yelled at by an impatient prospect.
- Use BARTS. Five gut checks before anyone designs anything:
- Budget — Can they afford the system?
- Authority — Are they empowered to make the purchase decision?
- Revenue — Will the project be profitable for the company?
- Timeframe — Can we hit the client’s deadline?
- Solution — Do we have something we can comfortably deliver and stand behind?
We’re not going to fully solve the need to handle 100% of prospect inquiries flawlessly anytime soon. Maybe the Caribbean inquiry landed on me because I was the best avatar for it. This was a prospect who knew he could book online through our website, but instead asked my friend if he knew anyone at Livewire he could get a warm introduction to. That persona likes talking to the person where the buck stops. Maybe the answer is that I can’t replace that, nor would I want to.
Also by Henry Clifford: AI Hack #541: The Gap Between Reading and Doing Just Collapsed
What we can do is sharpen our team’s ability to politely reframe the conversation and get the prospect ratcheted properly into our workflow instead of letting it spin out of control while we backpedal.
What are you doing to help your people pleasers engage with strong customer personalities?
Stay frosty, and see you in the field.
