Anytime you ask someone — a customer, investor, future business partner — for their precious time or money, you MUST know this:
Their challenge or pain point. Their goal or strong desire.
Yep, getting straight into Tip #1
I had a convo with a fellow founder who has a startup and was running an idea by me. He needed investors for an opportunity he had, and while he made valid points and was clearly passionate about this project, I knew right away he would not secure the private funding he was after. Not because his idea wasn’t good. Not because he wasn’t trustworthy. It was much simpler than that. It simply came down to incentive. Or in his case, a not yet clearly defined one.
The private investors he was seeking funding from were indeed financially able. But the one question I had was, “Yeah, but why? Why would they want to give you all that money? Why should they?” He started to tell me about the ROI and the vision he had, but, as a former quota-carrying sales professional and a current business owner, I knew none of that mattered without a clear answer to one question: Does this solve a real problem they have right now — or help them hit a goal they actually care about? Unless he knew what of the above would truly motivate this investor to part ways with a cool 3 mil, no dice.
Why does this matter? Think about it: As a consumer, anytime you’ve ever made a significant investment — a car, a home, education, an emergency room visit — there was a clear reason driving it. A problem. A need. Something at stake. Your customers are in the same position.
My strong advice: if you’re positioning an idea, product, or service to someone, you have to tailor it to why it matters to them — and what’s at stake if they don’t act. Take the time to understand the problem they’re facing and how what you have solves it. Find out what goal they’re chasing and how your opportunity gets them there. Now, I know that’s more work upfront. But skipping this step doesn’t save you time; it costs you the yes.
It needs to matter to them. That’s the difference between a delayed yes and a permanent no.
Similarly, Tip #2: Don’t assume you know what motivates your team. Take the time to find out.
It’s easy to – scratch that – it’s lazy to assume that just because you manage a team of sales reps, for example, you automatically know what drives them. You assume it’s money. After all, what other reason would someone put themselves through the torment of a sales career if not for the major financial reward, right? Wrong. Or at least, not always the whole story.
If I were a sales manager today, one of the questions I’d ask during the hiring process would be this:
If I were to create a spiff just for you, what prize would make it worth your effort?
Unplanned PTO day? Eight no-questions-asked WFH days for a month? Leave one hour early every Wednesday for a quarter?
Notice how none of these mention money. These are salespeople after all – they make money all day long. Might it be more exhilarating to put all their over-and-beyond effort into something specific they actually want? A $100 Visa gift card is still a win, don’t get me wrong. But would I work overtime for it? Probably not. Would I put in extra hours for an all-expenses-paid trip to San Diego booked from Thursday through Monday? Or a full week off next month with complete territory coverage guaranteed? Um, yeah. You wouldn’t offer Steph Curry a bonus check to go for 40 points. But fly his entire family out courtside and watch what happens.
Whatever your team’s flavor is, find that out. And get creative, create a spiff with them. Like, ‘Hey Trevor, if your team hits their quarterly goal four weeks early, I’ve got two hospitality tickets to the Liverpool match with your name on them.’ Or ‘Hey Laura, if you close 3 more opportunities above $45K each, I’ll give you one free mother and baby swimming class for 1 month on company time.’
This is the stuff that works and creates loyalty beyond what any Visa gift card ever could.
Tip #3: Yes, you’re the boss. But is control the same as leadership?
An executive whom I respect — let’s call her Jewell — came to me for advice one afternoon. She wondered how best to establish a clearer boundary with her newest employee, who’d been developing a casual cadence with her that made her a little uneasy. Now, this wasn’t the first time Jewell had mentioned this employee to me, and from everything I’d heard, this person was a perfect fit within the organization. To me, the read was simple: this employee wasn’t being disrespectful. They were comfortable. And from what they told Jewell, this was their first time having a boss like her — someone they genuinely admired for her leadership, her personality, even her fashion sense. So the casual vibe wasn’t a lack of respect for her position. It was an expression of appreciation for it. And the feeling was mutual. Jewell loved this person’s energy, enthusiasm, and upbeat vibe.
So I gently asked her: What is it that’s making you feel you need to draw a firmer boundary here?
Have you noticed in yourself or in someone you report to or even live with, a strong clutch on control? Because if you really sat with it, my guess is none of you mean any harm by it.
Here’s what I’ve learned: sometimes we mistake leadership for control. And our need for control is rarely about the situation in front of us; it almost always traces back to something much older. In Jewell’s case, it had nothing to do with her wonderful new employee who adores her and feels so relaxed around her because she actually respects and treats them well. It was a classic trauma response. And I don’t mean that judgmentally — we all have them. But it is our responsibility to address them, not project them.
So if you ever find yourself in a similar spot, my advice? Start there. Give yourself some grace. And let homegirl be.
Tip #4: If your team has low morale, making them work for some reward is not it. Consider a unity challenge instead.
I was speaking to a new officer in the military whose platoon kept coming in last place for certain field training events. Naturally, the unit felt down about this, but what could the officer do? It wasn’t their fault that the unit didn’t carry the physical strength to succeed. The way I saw it was they had two choices: Option A, go the ‘well you tried’ route and hope things change. Option B, take the focus off the loss entirely and find something they could actually win — together. Like a team fitness or conditioning challenge. Something everyone could do together every day before the next event. Nothing obnoxious, but something people would actually enjoy, while they’re pushing themselves, and even feel motivated to do.
I suggested the officer start a group thread with a fun kickoff message to launch the challenge — then keep the energy going with encouraging comments and photos throughout. Would it take a bit more effort upfront? Sure, but what would it be worth to have their platoon overcome this together, while getting stronger in the process as a unit — physically, mentally, and relationally, too? And pass those darn events for a change? My guess is a lot.
More work doesn’t always equal more reward. My advice: when your team is stuck in a losing streak, don’t pile on more pressure — change the game entirely. Give them something to win at together, and watch what that does for their confidence and their results. Get creative. It works.
Tip #5: Be the brunette in a room full of blondes
I was chatting with a payroll specialist one weekend who was confiding in me about an ongoing situation with her boss — one where she’d been holding back, playing it safe, staying quiet when she probably shouldn’t have. At some point in our conversation, something shifted. She said it herself: people respect you more when you speak your mind, even if no one else agrees or wants to hear it. And she was right. That’s when I came up with this analogy — Be the brunette in a room full of blondes. She happens to be a brunette, and so, sure, it was a little tailored, but my point is universal.
If you walk into a room of hundreds of blonde-haired people and spot just one brunette, who is by default the most interesting person there? The brunette. Simply because she stands out. You instantly want to know her story. How did she get here? Who is she? There’s clearly a type, so how did she beat the odds? Homegirl must be pretty special, considering there is literally no one else like her in the room, right?
Why is this important: Just because you go against the grain in some way – be it in how you dress, how you speak, how you perceive, how you contribute – doesn’t mean you should conceal it. My advice to you is if you’re special, so be it. Let the world know. Not because you’re arrogant. But because you have a point of view worth sharing, worth listening to, and definitely worth being taken seriously, regardless of your title or your difference.
So, be the guy with the beard when everyone else is clean-shaven, the dude with an afro when everyone else has a fade, or yes, the lone brunette in a room full of blondes. I’m way into hair, can you tell?
Your difference is what makes your contribution that much more valuable. We are not sheep, people. We are interesting, capable, and one of a kind. Let em know.
What was your favorite tip? Or, better yet, which tip made you go, ‘huh, I hadn’t thought of it that way’? Let me know in the comments.
A note from Erin: Thank you for being here! If these ideas or perspectives resonate with you, I’d love for you to subscribe or share them with someone you care about. If you’re looking to make a change or when the time feels right, I’m here to help. Check out my “WORK WITH ME” page to explore how we can work together—or swing by my “CONTACT” page to say hello, ask a question, or start a conversation.
