The Work Advice that Changed My Life

And ended up changing many more lives, too

Welcome back to The Workaround. I’m Bob 👋

You’re in good company with over 11,000 fellow entrepreneurs and innovators who follow my stories from a career in tech startups and corporate innovation.

I’m here to make you think, smile, and discover a shortcut to success or a trap to avoid.

Listen by hitting the play button above or using your favorite podcast app. Or listen and watch on YouTube.

When we are ready to listen, the universe picks someone to be a vessel for the message we need.

I recently heard a story from a veteran management consultant about being a rookie on the job many years ago…

She was on an early, high-pressure assignment, feeling stressed about whether she would be able to assist her client in an industry with which she had no prior experience. At one point, her more experienced manager saw the fear in her eyes and said:

“Being a consultant is like being a tour guide in a country you've never been to before. You just have to study the guidebook the day before everyone else does."

This handful of words gave her the perspective and confidence she needed, and she would go on to repeat them to many junior employees on her teams over the years.

Specific advice, offered early in our careers, can help us better perceive reality and adjust our course in a way that significantly enhances our potential for success.

This story brought me back to the best advice I ever received. It has shaped me into who I am today, far beyond business. Yet only now do I realize why I was able to hear it back then.

Starting at the Finale

It’s May 1998, and I’m staying at my friends’ home in Cincinnati, Ohio. It’s the summer before the second year of my MBA program, and in four days, I start my internship in marketing at Procter & Gamble. It’s Thursday, and I’ve joined them for a big party to watch the last episode of Seinfeld.

At the party, I meet Ann, who will be my manager for the summer. I find her to be an interesting mix of smiles and seriousness. She has recently been promoted after a few years at the company, and I will be the first person she has managed. Ann seems a little nervous about her new job and responsibilities.

But I’m much more nervous, as I’ve got what feels like my whole future riding on this summer job. My wife is still in New York City, hunting mice in our crappy, expensive little apartment. We’ve borrowed a lot for my MBA program before our undergrad loans are even paid off.

While nothing is guaranteed, there is buzz among the interns that performing well over the summer should lead to an offer to return full-time after graduation. I would love to come back and tell my wife that the sacrifice was worthwhile, and spend my second year of school with low stress.

I head off to my first day of work and begin onboarding with Ann. She quickly addresses my hope that there is an offer waiting at the end of my three months. But she warns me that I’ve got to finish my projects on time in order to get it. Then she walks through the four projects on my plate…

Do you remember being in college and the first week in class, when each professor shares the syllabus? It’s a massive list of quizzes, tests, homework assignments, written papers, and group projects. Each semester, I’d be in a daze for the first few weeks, wondering how I could get everything done.

That’s what I feel like now, with much higher stakes. I’ve got to do direct mail pieces, coupons, and a PR kit. I’ve never managed anything like this before, and they sure sound like they will take a while.

The good news is that I’ve got a design agency assigned to help me produce everything. The bad news is that they can’t kick the projects off for another week. This leaves me sitting…and stewing. I don’t have many days to work with, and what’s their schedule problem?

Words of Wisdom

I walk into Ann's office to share my concern with the agency. I tell her that I’m worried about my timeline and share my frustration. I say something like, “We’re the clients here. Don’t they understand we’ve got to get this moving?”

Ann smiles and takes a deep breath. She has a look on her face that I’ve seen before from patient teachers. She says:

“Here’s how you need to think about working with your agencies: They don’t work for you. You work for them.”

For a few seconds, I’m dumbfounded. What the hell is she talking about? This sounds idiotic. But then Ann saves me from myself by explaining:

“Your agencies and other business partners are critical to your success. They have skills that you lack. You can’t do the work they do. They also work on multiple projects and clients. If you treat them well, they will prioritize your work and bring even more creative energy. So it’s 100% in your interest to support them.”

I understood Ann, but it takes me a few days to let her advice sink in. Those days also gave me time to get my shit together before the kickoff meeting with the design agency. I come up with a plan.

My agency account lead, Lori, arrives at our office with a designer and junior project manager in tow. We sit down, and I proceed to lay it all out on the line:

“Look, I know nothing here. This is my first time in a marketing job. I need to finish my projects by the end of the summer to get this job. Do you think we can hit this deadline? How can I help you help me?”

Lori is surprised at first, but then settles back into a smile. She says, “Don’t worry, Bob, we can get it done, and we’re going to get you that offer.”

I relax, and we roll up our sleeves. In the weeks ahead, we produce great work together and deliver before my deadlines. Ann is excited to extend my offer, and I can’t wait to return and work for her again next year.

Servant Leader Mode Unlocked

Seeing this strategy work turned it into a model for the rest of my career. It was like a secret hack that we certainly didn’t learn in business school. It became my model for working with vendors of all kinds, both at work and in my home life.

When I onboarded my first direct report, I told him “I work for you”—then passed forward the advice that Ann gave me long ago. And I applied this mindset in my first CEO role, onboarding new hires by showing them how we flipped the organizational chart upside down.

Not only does this mental model help enroll and excite people to do great work for your business, but it ensures that you are scaling yourself. When the leader thinks they need to touch everything, people stop thinking for themselves. But when a leader admits they aren’t the expert and views their role as empowering others, they create an environment where every employee can work wonders.

Most people call this Servant Leadership. For me, it’s part of an overall approach to building a High-Performance Organization.

Once we see this model work its magic, we lean into it even further. We listen more closely, study human nature, and develop novel organizational systems that eliminate fear and foster trust.

And then we start to hear our teammates share our words back to us…

As I prepared to write this post, a little wink from the universe arrived in a LinkedIn post by my friend, Molly, who worked on my strategy team in my agency days:

I don’t remember saying this to Molly years ago, but I’m sure I did—because it’s what I felt then and now.

Ironically, my favorite compliments are when people repeat back something I said to them years ago—comments that stuck in their minds at the moment and set them on a different direction in work and life. It's always surprising to hear this, and a little scary. Words are spells…

Magic is Real

Only now, 27 years after hearing that advice from Ann, do I understand why they worked a spell on me the way they did. It’s the most interesting thing about re-telling stories here—I learn something new each time…

I was young and knew nothing about marketing. But I was eager to learn, and desperate for that job offer. And Ann’s advice was delivered with respect and care.

My Ego defenses were down. This allowed me to be in listening mode, and I heard the truth I so needed to hear.

And with the success of this new approach, I kept those ego walls from reforming. This is the mentality that helps us see our jobs as serving others and trusting that things will work out for the best when we lead with love rather than fear.

Note: It doesn’t take a brilliant leader or spiritual guru to speak the words you need to hear. When you need to hear them, and when your ego softens to allow them through, they can be hiding in plain sight.

Today, I receive invaluable words of advice from the strangest people and places. When this happens, I often think of the character, Sybill Trelawney, from the Harry Potter books. She’s the Professor of Divination who can’t see the future when it’s in front of her face—except for that one time when she is right, and Harry hears her.¹

The Greeks got this from the Oracle at Delphi. Some people find what they need to know about themselves in personality tests, dream interpretation, tarot cards, or astrology. When it works, it’s not hocus pocus, but rather our unconscious selves seeing and mirroring the truth back to us.

Great leaders realize their words can be spells. We can use threatening words to motivate people through fear. Or we can lead with a spirit of love. Either way, we will affect business performance and impact the broader lives of our employees.

I wonder if I would be different today if Ann’s advice came from fear instead. What if she said something like, “You need to threaten that you’ll move your business elsewhere if they don’t deliver.” I’ve seen people’s careers poisoned by their first bosses’ awful words.

Would I have gotten the internship? Founded companies? Formed the same friendships and be the same husband and father? What words would I be writing here today? I’ll never know…

But now I know this: We must choose our words wisely, for they might change someone’s life.

If you like my writing, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏

---

How we might work together…

• Fleet is our holding company for services businesses. We invest in leaders ready to start their own companies (we also do some M&A). If this might be you, hit my Office Hours link.

• A2 Influence is our content development agency that helps some of the biggest brands and retailers create and distribute authentic content at scale, including social+influencer. CEO Rob Reinfeld would love to share our approach.

• Revelin is our consulting practice that helps with revenue alignment, growth management, and other RevOps functions. CEO Jess Shuman is standing by to share a no-cost assessment of your business.

• Feel free to schedule a chat during my Office Hours to discuss questions, feedback, networking, or any other topic. Seriously, any topic! You can also reach me on LinkedIn or by email.

---

BONUS: Cool Content of the Week

A little something I found meaningful. You might agree…

Remarks on AI from Neal Stephenson

Speaking of voices from the future…I’ve raved before here about Neal Stephenson, and I’m doing it again.

If you want to make bets on the future, you could do a lot worse than consulting the most popular science-fiction works. I recently re-read Stephenson’s The Diamond Age, a vision of a high-tech, AI-driven future that feels remarkably close to reality today, despite being written almost 30 years ago.

Neal writes about the present and future from a non-fiction perspective on his Substack. This week, he shared a summary of his view on AI from a panel he spoke on in New Zealand recently. As expected, it’s unique and fascinating. In particular, Stephensen suggests that we’ll be unleashing an ecosystem of entities, and he hopes that competition will keep them in check. He also warns that augmentation can be powerful, unless it leads to the amputation of our previous skills and abilities.

Remarks on AI from NZ

1. For a more real-time cultural example, the book The You You Are in Severance is a great one :)