Q&A with HPA Partner, Richard Berger
In this Q&A, Richard Berger reflects on how his view of career success has evolved, from chasing titles. Drawing on his experience across corporations, startups, and consulting, Richard shares lessons on patience, preparation, and building a career that endures.
Q: Early in your career, what did you think success looked like?
In the beginning, when I was most influenced by my peer group, I thought success was mostly about pace and prestige: getting promoted quickly, landing the “quarterback” roles, and being on the fast path to promotion. I pushed for bigger jobs and higher-visibility assignments, sometimes simply because they looked more exciting from the outside. I was too focused on how fast I could move, and not enough on whether I was really playing to my comparative strengths.
Q: Looking back, what would you tell your younger self about those choices?
I would ask, “Where do you actually have an edge?” and “Are you building on that, or chasing something that just sounds cooler?” In a few cases, I moved toward roles that were more glamorous but not where I had a true competitive advantage. Over time, I have come to appreciate that sometimes being a bigger fish in a smaller pond is the better choice. It is usually smarter to lean into the areas where you are genuinely differentiated than to sprint toward the shiniest opportunity. When you bring some unique skill or capability, you will likely enjoy the work more and be more valued.
Q: You have worked in large corporations, startups, and consulting. What did that mix teach you?
Each environment has its own reality. In big companies, you get strong training and resources, but early on you can be several layers removed from meaningful impact. In startups, you see the consequences of your decisions every day, but you often operate with limited data and support. Consulting forces you to drop into new situations, get smart quickly, and help clients move from theory to implementation. Across those experiences, the consistent lesson is that strategy only matters if it can survive contact with the real world, customers, front-line teams, and practical constraints.
Q: How do those lessons show up in your work at HighPoint Associates today?
At HighPoint, we place a premium on people who have “been there and done that” before they show up in a client’s conference room. My earlier roles taught me how frustrating it is when smart people present elegant answers that do not fully reflect operational reality. That is why our model centers on seasoned practitioners who bring both analytical skill and the scar tissue of having run businesses. We want our recommendations to be practical enough that clients can and want to implement them, not just admire the slides.
Q: How is HighPoint’s approach different from what you saw earlier in your consulting career?
Earlier in my consulting career, there were times when teams were clearly learning on the client’s dime. You had bright people, but not always with deep, relevant operating experience. Thus, time to true impact was sometimes longer than optimal.
At HighPoint, we work hard to avoid that. The people leading our engagements have years of line responsibility in roles similar to our clients, such as P&L ownership or functional leadership. That creates a different kind of conversation. Instead of debating whether something makes sense in theory, you have someone who can say, “Here is how this actually played out when we tried it, here is what surprised us, and here is how we can reduce the risk for you and your team on this effort.”
Q: You have talked about the risks of overconfidence in consulting. What do you mean by that?
In some traditional models, there is always quiet pressure to project confidence at all times, even when you are still climbing the learning curve. That can tempt people to act like experts in situations where they are not, which is dangerous for the client and uncomfortable for the consultant. Early in my consulting career, I had moments where the stakes were high, the client was paying a lot, and our team was still learning the nuances of the sector. I learned it is far better to be curious, honest about what you are learning, and to draw on real operating experience where you have it, rather than acting as if you have all the answers.
Q: When you think about HighPoint’s evolution over the last decade, what stands out?
The scale has changed, but the core value proposition has held up and, if anything, become more relevant. We now work with larger clients on more complex engagements and support them over longer periods of time. At the same time, clients have become more familiar with different consulting models. Many have tried both traditional firms and alternatives, so they are more open to the idea that who is on the project matters more than the logo on the cover page. That has allowed us to build long-term relationships and see the impact of our work across multiple phases, not just a single project.
Q: What do you now see as the most important ingredients for a fulfilling career?
Patience, preparation, and relationships. Early on, it is tempting to measure yourself by how quickly you are advancing compared to others. Over a longer horizon, better questions are: Am I still learning? Am I working with people I respect and enjoy? Am I building a reputation that makes people want to call me back? I encourage younger professionals to focus less on speed and more on becoming a more complete professional year after year. If you keep showing up prepared, keep listening, and keep helping others, good opportunities tend to find you.
Q: You emphasize relationships a lot. How have they shaped your path?
Some of the most rewarding moments in my career have been when former colleagues became clients or partners years later. People I worked for in my first job have later trusted me with significant projects, and former peers have become sponsors and sounding boards. Those are not accidents. They come from how you show up day after day, whether you are reliable, thoughtful, and generous with your help. Careers are long and surprisingly circular. You see people again and again in different roles. If you invest in those relationships early and try to pay it forward, the benefits compound in ways that are hard to predict but very real.
