Different Questions
/Looking back, what questions do I wish someone had asked me at the key moments in my career?
Getting Started
When I graduated from college, I wasn't thinking about building a career. I was focused on getting my first real job, putting my new computer science degree to work, earning a good salary, and beginning my life on my own. I considered several opportunities around the country, ultimately accepting a position in California. It felt like the beginning of something exciting, full of possibility and independence.
Looking back...
At that time, i was simply getting started. I wasn't trying to discover who I wanted to become. I was trying to launch a life.
The question I wish someone had asked me
What else feels important about this decision that isn't easy to explain?
Making It
Within my first year or two after graduating from college, I had developed a vision of what it meant to have "made it." I described it to a colleague: an office on "mahogany row," an executive secretary, expensive suits and shoes, and my name on the door: A. Howard Ingram. It was less about the work itself and more about the trappings. Leadership and executive life were still ideas more than lived experience.
Looking back...
At that point in my career, advancement meant becoming the kind of person I imagined successful people to be. It was about being someone who had "made it."
The question I wish someone had asked me
How do you imagine your life will be different once you've "made it"?
Being Seen
As my technical skills developed, so did the opportunities to make a broader impact. I presented a paper with one of our clients at a national user symposium, which caught the attention of another company and led to an invitation to interview. When I accepted the new position, a senior executive at the company I was leaving told me they had "big plans" for me. My immediate response was, "I wish you'd told me sooner."
Looking back...
Advancement meant being recognized for the unique contribution I could make. I hadn't yet realized how important it was to know that people saw not just what I did, but what I was capable of becoming.
The question I wish someone had asked me
When you want someone to notice you, what do you most hope they're noticing?
Operations!
As my career progressed, I found myself increasingly drawn to operational leadership. I enjoyed solving organizational problems, improving processes, and helping people and teams work together more effectively. I proposed creating an administrative unit for our district and was given the opportunity to build and lead it in addition to my technical responsibilities. That role eventually led to a promotion as Regional Operations Manager, and then appointment to a team reengineering divisions.
Looking back...
Advancement meant finding work where I could make a meaningful difference. I was beginning to recognize that I was energized less by technology itself and more by improving the way organizations and people and systems worked together.
The question I wish someone had asked me
What kind of work leaves you feeling most alive at the end of the day?
Integration
After leaving corporate life, I felt certain of one thing: I didn’t want to work for a large corporation again. I tried starting my own handyman business while doing some consulting on the side. Eventually one of my clients, a growing technology company, invited me to join them. For nearly a year I said no. When I finally accepted, it wasn't just because of the salary and benefits. The owner had embraced me fully as a gay man, even attending one of my chorus concerts with his girlfriend.
Looking back...
Advancement meant finding a place where more of who I was could come to work with me. I was beginning to understand that belonging and alignment weren't nice extras. They shaped the kind of work I could do and the kind of leader I could be.
The question I wish someone had asked me
What parts of yourself need to be welcomed in order for you to do your best work?
Finally, Vice President
Years earlier, that title would have felt like proof that I had made it. Instead, it became one of the most important moments of awareness in my career. The role carried responsibility, but not the agency I believed was necessary to do it well. After a time, I made the difficult decision to step back into a senior project management role, where I found myself with more alignment, more influence, and ultimately more satisfaction.
Looking back...
Becoming Vice President challenged everything I thought that vision represented. I realized the title mattered less than having the trust, influence, and agency to fulfill the responsibility it carried.
The question I wish someone had asked me
What needs to be true for the VP role to become the place where you can do your best work?
The Rest of the Pie
Shortly after I moved to Boston, I joined the Boston Gay Men's Chorus. I expected to sing. Before long I found myself volunteering, serving on committees, joining the Board, and stepping into leadership roles. None of it came with a paycheck or recognition. I simply enjoyed contributing, performing, helping the organization succeed, and being part of a community that mattered deeply to me.
Looking back...
I had spent years focusing on the "work" slice of the pie. As I engaged more fully with music, community, spirituality, sexuality, and identity, I became a different leader at work as well. My career wasn't separate from the rest of my life. It was being shaped by it.
The question I wish someone had asked me
Where do you most want to invest your gifts, regardless of whether you are paid for them?
Today
At the present moment I’m a leadership coach supporting the LGBTQ+ community. I care about awareness. About helping people notice the stories they're living before those stories quietly become their identity. It's part of why I write and why I coach. Not to tell people what their next chapter should be, but to ask questions that help people become more aware of the one they're living now, and the choices they have.
The questions that mattered to me at twenty-two weren't the questions I needed at forty-five. They aren't the questions I'm asking myself today.
I'm less interested in climbing higher than in living more fully. Less interested in reaching the next milestone than in understanding the person who's reaching for it. Less interested in finding the right answers than in asking better questions.
Looking back…
Revisiting all these stories, I don't wish I'd followed a different path. I do wish I'd asked these questions sooner. Not because they would have changed every decision, but because they might have helped me understand the person making those decisions a little more clearly.
I don't see a career that unfolded according to plan. I see a life that kept inviting me to become someone new.
The question I wish someone had asked me
Who are you becoming today?
Now, Your Story
You are professional, smart, capable, and successful by almost every external measure. You have likely reached this point in your career and life by being adaptable, resilient, and exceptionally good at navigating complexity. You’re still making choices. You’re still evolving. The questions you’re asking are different now. And that’s okay.
Looking back…
You sense there could be more to success. You want your work and life to feel more meaningful, and more fully your own.
The question I would ask you now
Who are you becoming today?