Isaac MacDonald of Trepwise On 5 Tips For A Successful Performance Management Process
An Interview with Rachel Kline
Performance Management could also just be called Management — it is the day-in, day-out work of learning from and with your team members. So often people think of it as a single meeting or report, but good performance management requires coaching, follow-up, and consistent communication.
Performance management is notoriously difficult to get right — but not impossible. In this series we speak with experts to get their insights into creating an effective performance management system. As a part of this series, we had the pleasure of interviewing Isaac MacDonald.
Isaac MacDonald is the Director of Planning & Impact at Trepwise, a strategy consulting firm. He has worked with more than 100 mission-driven organizations to develop strategic plans and improve their organizational effectiveness, including The Jazz & Heritage Festival & Foundation, the Orleans Public Defender’s Office, and Studio BE.
Isaac graduated with a degree in Urban Studies from Brown University in 2015, after which he was a Fellow with Venture for America and a member of the New Leaders Council, Class of 2021. He resides near Bayou St. John in New Orleans, LA.
Thank you so much for your time! I know you are a very busy person. Before we dive in, our readers would love to get to know you a bit better. Can you tell us a bit about your backstory and how you got started?
I guess you could say I really got started doing the work I’m doing today back when I was in college. I was getting a degree in Urban Studies — zooming out to learn about how policy and the built environment shape the places we inhabit, but also zooming in to try to understand how these systems impact people and how they navigate them. In my senior year, I traveled to Medellin, Colombia, to research a very successful public transportation initiative. The basic takeaway of the entire thesis was that process matters, and that public participation matters. And that’s the work I’m still doing today.
After college I moved down to New Orleans and got a job at this early-stage consulting firm that was focused on organizational strategy and problem-solving that puts people at the center — and here I am, almost a decade later, still helping purpose-driven clients across multiple sectors to deepen their impact…and making work not suck.
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
When I first moved to New Orleans, my primary form of transit was this little old Vespa. Most of the time that wasn’t a problem for work because clients would come to our office, and nothing in the city is too far away. But one day I had a client meeting across town, and as I was scooting over there, the sky just opened up in classic Louisiana summer rainstorm fashion. I showed up to the client’s office soaked to the bone. They laughed at me a little but gave me a towel and eventually we continued with our planned agenda. It was a lesson that people are gracious — and probably also a lesson about knowing when it’s best to just reschedule a meeting.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?
When I was in high school, I became president of a regional Jewish youth group. The person in charge of the group at the time, Alexa Broida, was this amazing blend of organized and imaginative. Working with Alexa was the first opportunity I had to explore a question I still think about a lot in my work, which is discovering what it takes to build spaces where people can experience wonder and safely explore possibilities. At one of our events, we decided to audio record all of the participants reflecting on their “X factor” — the one thing that truly lights them up in the world — and then cut all the recordings together before the next day of programming. At 3am, when I was barely halfway through editing the recordings, I remember Alexa giving me two great pieces of advice: firstly, a reminder that it didn’t have to be perfect, and secondly, she basically said, “You chose this, so go execute it.” I wrapped it up, got two hours of sleep, and was able to pull off a very memorable event the next day.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
It’s got to be Soren Kierkegaard’s “Life is not a problem to be solved but a reality to be experienced.” I think part of being “high-performing” in our society is to get really good at framing and solving problems, which can be great. But the inverse is that it can become very easy to get overly focused on issue-spotting in our organizations, our networks, and our communities. The result is sitting in a mental model that makes your entire life an exercise in adding to and checking off an unlimited to-do list. A big thing I’ve actually learned living and working in New Orleans is the power of appreciative inquiry and the benefits of taking the time to experience life as it’s happening. We can easily be dulled to the human experience — its incredible highs and harrowing lows — if we’re always trying to “solve” ourselves and the world around us.
Thinking back on your own career, what would you tell your younger self?
1. Trust the people closest to the problem.
2. Assume those in power do not have a good reason for being there until proven otherwise.
3. There are surprising levers to changing systems if you look hard enough.
4. No one is coming to save us; we have to build the future we want.
Let’s now move to the central part of our interview. Why is performance management so tricky to get right?
I think the trickiness comes because performance management is wrapped up in so many deeply human concepts. The way we give feedback, evaluate, and reward one another is so tied up in our beliefs, our biases, and our idiosyncrasies as people. Not to mention that the repercussions are major — promotions, raises, terminations. These are things that really impact people’s lives.
Where do you see a lot of organizations go wrong with performance management?
I’d say I see two common ways that people go wrong with performance management. The first one is making it too complicated, whether that’s trying to develop a really sophisticated incentive package or trying to cascade a ton of organizational goals into individual goal-setting. The over-complication of the tools and processes is actually one of the main drivers of the other primary issue, which is that performance management is treated as a moment, not as an ongoing conversation and process. If it’s a herculean effort to get it done, then everybody just breathes a sigh of relief and waits to have another performance conversation 12 months later, which is the exact opposite of what should be happening.
In your experience and success, what are your top 5 tips for a successful performance management process? Please share a story or an example for each.
1. Include the WHAT and the HOW
It’s essential that team members know the set of skills and abilities that are expected of them and have a regular assessment of whether they are performing their job duties. Yet, if you focus only on this — the “what” and not the “how” — you’ll end up rewarding behavior that erodes your culture and, ultimately, your organizational performance. That’s why it’s best to incorporate an assessment of how people are living into the organization’s values as part of your process. For example, team members at our firm are evaluated on the behavior of “Analytical Thinking” and also the value of “Curiosity.” Kevin Wilkins, the founder of Trepwise, often talks about his time working in financial services, where the modus operandi was “just get it done, even if you leave bodies in the hallway.” I was always struck by the image of the metaphorical dead bodies lying there, conjured to represent unruly corporate jostling, but the point is clear: If you set up a culture where the only thing measured is goals and hard skills, you’ll learn the hard way that your system is missing a big part of what drives organizational and business success.
2. Identify and Celebrate Unique Talents
In his best-selling book Nine Lies About Work, Marcus Buckingham challenges conventional wisdom about growth and performance, writing that we shouldn’t necessarily be looking for people to be well-rounded because, in fact, “the best people are spiky.” That’s definitely what I’ve seen with the leaders of the organizations we work with — there is no recipe for being a great leader or a great employee, and the best performers are almost always all-stars at a few key things (i.e., “spikes”) that allow them to make a big impact. Performance Management systems are typically built to measure a broad set of criteria and then evaluate everyone against them. While this can be helpful to raise the floor of your team’s abilities, it can often lead not only to conversations with your employees that focus on weaknesses, but also, in the long term, it can lead to mediocrity by filtering out high-performing “spiky” people. The best systems identify, celebrate, and encourage people to unlock their unique potential. So, in your process, figure out how to not just focus on how your team can build skill where they’re lacking in ability but also to leverage their existing abilities to deepen their impact.
3. Solicit Feedback and Gather Diverse Perspectives
Gone are the days of the simple manager review. For a while now the typical tool that we’ve seen has been a “360” — an opportunity to get a holistic picture of your performance — which includes a self-assessment as well as perspectives from superiors, peers, and direct reports. Now, this doesn’t have to be everyone reviewing everyone else. You should figure out what the right sample might be based on the size of your organization. If you’re evaluating an organizational leader, consider effective ways to capture the perspectives of both the Board of Directors and the staff that work directly with and under their leadership. Often, we find that people are harder on themselves than their peers, and it’s helpful for employees to see where gaps might exist in self-perception versus how others think of them.
4. Center Equity by Being Clear and Intentional
Our firm has been working with an incredible Diversity, Equity & Inclusion consultant, Rachel Vicente, and one of her big pieces of advice was that inequity often persists not because of what is written down, but rather because of what is not written down. Performance Management and Advancement criteria should be explicit about what is expected of all employees — and also at different role levels, so team members know what it takes to advance. The first step is being clear and explicit about what it means to perform in your org. As you’re doing so, it can be helpful to interrogate the underlying assumptions that go into a given criteria — often it may be imbued with biases about race or gender. It can be helpful to use tools like the characteristics of White Supremacy Culture; try to identify and root these out. For example, we’ve been trying to reduce the feeling of “sense of urgency” in our workplace, and we found that a few of the variables we were assessing were contributing to that. Finally, instead of just trying to do harm reduction in relation to bias in your performance management system, consider centering the behaviors and values you want to see. Could you assess the ability to notice and address power dynamics in meetings? Could you ask in your 360 whether colleagues feel that their team member is creating spaces where they and others feel valued and able to be themselves? Define the inclusive culture you want and start baking it into your systems!
5. Create Multiple Touchpoints as Part of a Year-Round Effort
Performance Management could also just be called Management — it is the day-in, day-out work of learning from and with your team members. So often people think of it as a single meeting or report, but good performance management requires coaching, follow-up, and consistent communication. (It should also be clear how the performance management process aligns with advancement and compensation.) At Trepwise, we had been running our system with annual 360s and 6-month check-ins for a while, but we found that team members were still going for long periods of time without knowing how they were performing or measuring up. We decided to launch a mentorship program where every team member would meet monthly with a leadership team member to talk about their professional desires (inside and outside the organization), their goals, and their reflections on performance and needed support.
How do you approach performance management in your organization? Do you tie it to compensation, for example?
New team members receive 30- and 90-day check-ins. Then, our ongoing performance management assessment is divided into Skills/Abilities and Behaviors. Team members receive a “360 review” annually that includes qualitative and quantitative feedback, as well as a 6-month check-in that pulls qualitative insights from a selection of team members who work most closely with them. Compensation is not directly tied to scores, but we schedule annual reviews of compensation for employees to coincide with performance reviews so that we have a shared set of information to use to make decisions and have compensation conversations.
Which tools do you use for your performance management?
We use a tool called the Predictive Index to guide our hiring and team collaboration discussions. We use Surveymonkey to collect team feedback and then synthesize the results into a written report. One tool I recommend frequently to clients is the 2x2, a tool that can be used at least quarterly or even more regularly between team members and their managers to develop two-way feedback and provide space for constructive feedback specifically on performance and management. And, when in doubt, you can use Radical Candor to help incentivize a culture of feedback and transparency.
How do you measure and improve your performance management process?
At Trepwise, we have a “culture survey” that we issue a few times a year where we ask people how they’re feeling about a number of different aspects of our workplace, including performance management. We also frequently revisit our values and talk about bringing them to life. Moving forward, we’re thinking about how to embed more measurable goals into performance management, like client satisfaction or project profitability — but any time we introduce something new into our assessment, we like to have a trial period where people are presented with the information prior to being assessed against it in the following round of reviews.
We are very blessed to have some of the biggest names in Business, VC Funding, Sports, and Entertainment read this column. Is there a person in the world whom you would love to have a private lunch with, and why? He or she might just see this.
It’s gotta be Beyonce. Beyonce, if you’re reading this and have gotten this far, then you have a lot more free time on the Renaissance Tour than I would have expected. Please call me anytime.
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Thank you so much for sharing these important insights. We wish you continued success and good health!
