Ep 173: Mentorship Matters

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When I think back on the early days of my career, I can remember how many things I didn’t know — and maybe even more clearly, how many things I thought I knew but clearly didn’t. There were decisions I made with complete confidence that, in hindsight, probably should have come with a warning label. Somehow, through a combination of luck, patience from others, and the occasional eyeroll, I kept moving forward. What’s interesting to me now isn’t just how much I’ve learned, but how I learned it. It’s easy to underestimate the value of those moments until you’re the one on the other side of the conversation and you have some responsibility of helping other people navigate the development of their careers. Welcome to Episode 173: Mentorship Matters.

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Today we are going to be talking about Mentorship stuff. I need to confess that most of what I am bringing to the conversation today reflects the time, effort, and energy that I have put into place with the mentorship program that exists within my own office.

Background jump to 4:29

“Setting the Table”
I never had a mentor – at least nothing formalized. The mentorship program in my current office began innocently enough – I just wanted to check in with the people who were listed as my direct reports, and things just kind of grew from there. For the first few years after a program was put into place, it was viewed with mixed results because not all mentors are the same and they don’t all put the same sort of value on the process.

Another consideration that has a significant impact on whether a mentorship program works is the access to information and experience. My position as a principal in my office gives me a perspective when talking to employees that bridges almost the entirety of the firm, in some ways, just because I have access to more information than other people.

People in my office who are in a mentor position, ask about what I do in my meetings. They are looking for something formalized which to be honest, I just led with what made sense to me and relied on my ability to listen and read the tone and tenor of the conversation. Ultimately, this is not a scalable method – which is reflected in the fact that there are just a few of us now that have maintained responsibility as mentors. Despite the fact that I know my “process” isn’t scalable, I am reluctant to give it up because I love being in this role because it allows me to stay connected to the people in my office and helps me understand how people are feeling … but as my other responsibilities grow, this is maybe not the best use of my time.

Mentorship Programs jump to 25:19

Creating a mentorship program became my goal after realizing how much I’d missed by never having a formal mentor. I began with informal check-ins to give everyone someone who truly understood their goals and aspirations. Before long, it was brought to my attention that only a handful of people enjoyed the benefits of these one-on-ones, leading to concerns about fairness. That’s when HR stepped in, asking me to formalize the process and to make this available to everyone. I soon discovered that being a mentor isn’t for everyone—some folks don’t have the right approach—and that experienced senior staff, though knowledgeable, are often short on time. Striking the right balance between strong mentors and available mentors became an immediate challenge.

I also came to see that authentic mentorship depends on structure: defined goals, recurring check-ins, and built-in accountability. I realized deeper discussions happen when meetings are planned, rather than squeezed in on the fly. In my experience, senior employees often look for strategic insights about the firm, while newer team members thrive on skill-building and confidence-boosting support. I work to address everyone’s needs by ensuring fairness, encouraging wide participation, and making thoughtful mentor-mentee matches. The effort can be complex, but I find that, at least for me personally based on how I go about building relationships during the mentor/mentee check-ins, enhanced firm culture and the improved retention make it all worthwhile.

You can and should formalize the mentorship program structure.

A successful program needs:

Clear goals (onboarding, leadership development, retention, satisfaction).
Defined expectations (monthly meetings, self-directed topics, progress check-ins).
Program infrastructure (mentor/mentee matching process, kickoff materials, guidebooks, optional prompts or topic suggestions, and evaluation metrics).
Accountability tools (quarterly feedback surveys, simple reporting of meeting frequency, optional group mentorship events).
Support from leadership (principals and owners need to endorse the program and set the tone).

What Makes a Good Mentor? jump to 31:51

The success of the program does depend on the people identified as mentors — but you can shape that success.

The mentor’s attitude and skill are pivotal. Andrew and I spent some time talking about the challenges that present themselves when you have people who want to be mentors, but the mentees associated with that mentor are less than enthusiastic about the pairing. As you can imagine, creates an entirely new set of challenges to address – it is hard to tell someone with the desire and capacity to be a mentor, but lack some other critical personality traits that allows for a successful connection to be made.

So where do you start?

Some senior staff are naturally empathetic and engaged — these are your anchor mentors.
Others may need development — you can offer mentor training sessions that include:
- How to listen effectively
- How to give constructive feedback
- How to guide without micromanaging
- The importance of consistency and follow-through
A good structure makes average mentors better, but a program with the wrong people in mentorship roles can flounder
Selection is key: pick mentors who are respected, patient, communicative, and invested in the firm’s future — not just the most senior or technically skilled individuals.

Why Mentorship Matters jump to 39:46

It was at this point in the podcast that I realized that we had worked through about 15% of the information I had brought to the conversation. I don’t really want this to be a two-part subject so I am just going to include the high-level talking point down below with summary of each section.

Developing Future Leaders

Enables emerging talent to learn leadership skills in a structured, low-risk setting.
Encourages mentees to take initiative, practice decision-making, and learn from feedback.
Exposes future leaders to the business and strategic aspects of running a firm.
Helps senior staff identify high-potential individuals for advanced roles.
Creates a long-term leadership pipeline critical for firm continuity.

From where I stand, mentorship isn’t just a tool for helping novices; it’s a springboard for cultivating tomorrow’s decision-makers. By giving folks a safe place to spread their wings, they’re more likely to take on challenges and sharpen the skills that set them apart. Over time, this guidance helps them see the bigger picture, inspires them to own their contributions, and reveals emerging leaders who will eventually uphold the firm’s vision and values when it’s their turn at the helm. There is a blog posts I wrote years ago titled “The Crummy Pillow Paradigm” that explains what it means to empower people to develop into future leaders. It might be one of the best posts I have ever written and is probably worth your time to check out.

Talent Retention and Loyalty

Signals the firm’s investment in each employee’s personal and professional growth.
Provides support during career inflection points, helping employees push through challenges.
Reduces burnout by offering perspective, encouragement, and practical advice.
Strengthens trust between junior and senior staff, fostering loyalty.
Makes the firm more attractive to prospective talent looking for mentorship-rich environments.

I know firsthand how feeling valued can turn a “maybe I’ll leave” into “this is where I belong.” Mentorship programs show employees that the firm isn’t just counting on them; it’s counting with them. This mutual investment builds loyalty and a sense of camaraderie, especially during rough patches or moments of transition. I’ve stuck around in roles precisely because someone took the time to nurture my career path, and I believe that kind of genuine support can transform job-hoppers into devoted team members.

Enhancing Employee Satisfaction

Increases confidence by offering reassurance and constructive feedback.
Cultivates a sense of belonging through ongoing, intentional interaction.
Helps employees see clear career pathways and long-term opportunities.
Provides a space for recognition, validation, and personal encouragement.
Fosters stronger relationships within the firm, making the workplace more rewarding.

When I think about what makes me excited to walk into work every day, it’s the feeling that I’m not walking alone. Mentorship—when done thoughtfully—becomes that steady hand on your shoulder. It boosts confidence by showing people they have both permission and support to grow. Beyond the immediate lift in morale, it lights a path forward, clarifies opportunities, and assures folks they have a true advocate cheering them on. In my opinion, it’s exactly this level of intentional engagement that makes a firm feel like home.

Strengthening Firm Culture

Encourages shared values through personal stories and lived examples.
Preserves institutional knowledge that might otherwise be lost over time.
Promotes consistency in client interactions and project delivery standards.
Reinforces collaboration and trust as core aspects of how the firm operates.
Provides a structured way to transmit the firm’s vision and strategic direction.

The best lessons I’ve learned weren’t in manuals—they were in casual chats with someone who’d been there before. By codifying these exchanges into formal mentorship, we ensure the firm’s culture, traditions, and unwritten wisdom live on. It also bolsters consistency in how we deliver projects and handle client relationships. Essentially, mentorship ties everyone together under the same banner, so we operate as one cohesive entity guided by shared values and a common vision.

Employee Benefits jump to 44:08

So let’s take a step back and look at this from the perspective of the employee…
You’ve got the skills, you’re doing the work—but there’s a sense that something’s missing. Maybe it’s direction. Maybe it’s a sounding board. Maybe it’s just the need to feel like you’re not figuring it all out on your own. That’s where mentorship makes all the difference. It’s not about having all the answers handed to you—it’s about having someone who knows the terrain walk alongside you for a while, helping you navigate the turns you didn’t see coming.

So why would an employee benefit from participating in a mentorship program? Here’s a few quick reasons:

Access to experience: Direct learning from someone who has been through similar challenges.
Career clarity: Guidance on licensure, advancement, and long-term career paths.
Confidence building: A safe space to ask questions and receive constructive feedback.
Expanded professional network: Introduction to senior leaders and exposure to different areas of practice.
Opportunities for visibility: The chance to stand out, take ownership of projects, and position oneself for promotion.

The truth is, no one does this alone. Even the most talented architects—which in my mind are the ones that are the most rounded—didn’t get there in a vacuum. They asked questions. They made connections. They had moments of doubt and people who talked them through it. Somewhere along the way, they were given the space to be seen. That’s what this is about. Not hand-holding, not shortcuts, but the right conditions for someone to step into who they’re capable of becoming. And if we can create more of those moments for more people? That’s where real progress happens.

Hypothetical jump to 53:19

Today’s question comes to you as part of a debate of which would be more irritating to the people around you.

You have the option to choose one of the following scenarios: You either have to wear wooden Dutch clogs all the time … or wheelies*.

C’mon … is there really a choice here?

*by the way, I just found out that these sorts of shoes are called “Heelies” *

It is not lost on me that someone who navigated almost the entirety of their career without any sort of recognized mentor would be here today talking mentorship – or perhaps that makes me entirely qualified to talk about why it matters. As I was trying to sum today’s conversation up, I am really just left thinking about two things – why this is good for me, and why I think it is good for the employee – and both are incredibly direct and clear. I enjoy the process of being a mentor because it helps me stay connected to the concerns and interests of the people that (at least at some level) I have some level of dominion over. I want these folks to achieve success and I feel like I can help them in a meaningful way to get there. From the employees viewpoint, participating in a mentorship program gives you access to to insight and information that can help guide you through some fairly significant moments of your professional life. When the mentor is in your same office, it’s kind of like meeting with the teacher. I am invested in the success of the growth and success of the people I meet with and if understanding their needs and passions helps them in anyway, that’s a win for the both of us.