Using Feedback Forcing Functions
We're all bad at sharing feedback, here's some systems that break the barriers
Welcome to the latest entry in The Workaround. You’re in good company with thousands of fellow entrepreneurs and innovators!
I’m Bob, your host. My mission here is to share personal, behind-the-scenes stories of the ups and downs of my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…

I was a guest at a health-tech startup's annual offsite a few weeks ago. Its CEO, Daniel, brought together me and two other experienced founders to share our stories of scaling up our companies. He and his group of 40 employees (up from 25 last year) had lots of questions—and likely a few worries that the magical culture of their smaller business would be threatened as they grew.
Much discussion revolved around their desire for feedback. Knowing how we’re doing is important in any job. To borrow from my Ship analogy, we want to ensure we are effective crew members. If we are sensing positive signals, we’ll feel safe and keep performing. Otherwise, we’ll fear getting walked off the plank.
The need for feedback is even higher in small, high-growth startups. Our roles constantly change, so traditional job descriptions and performance measures are mostly meaningless. In our panel discussion, for example, almost no one raised their hands when one of us asked, “Who here is still doing what their original job description included?”
With more employees, forging relationships becomes harder. Remote work makes getting to know each other more challenging. All of this means feedback is more important yet more difficult to share.
So, the question was posed to me: How can we maintain the culture of feedback that is a strength today? My answer: You’ve got to force it with functions and processes…
People Are Tricky
Let’s first get this moose on the table: People generally hate giving feedback.
So much of our social programming steers us away from hard conversations. We don’t like confrontations, we don’t want to make people feel bad, and we can be defensive about critiques of our work. Things can be said and/or heard the wrong way, hurting feelings and damaging relationships. And we can’t “break up” with a manager or co-worker without quitting the company.
Thus, we take the path of least resistance. One-on-ones touch on project updates if they still happen. A major client is lost, but there is no debrief on what could have happened differently. The quarterly number is missed, and people look around, waiting for an axe to fall. Everyone wonders if we will talk about this, but there never seems to be enough time, and it’s too sensitive to spark a discussion thread on Slack.
Maybe we occasionally say “Great job!” or host a celebratory (mandatory) happy hour. We save all our “opportunity area” feedback for annual personnel reviews and peer feedback requests. Cue the anger and tears as people are surprised by learning that they’ve spent the past year doing bad work and pissing people off.
The solution? Create structures that break us out of our normal daily routine and become excuses to have real, meaningful conversations about our personal, team, and company performance.
12 Examples of Feedback Functions
What I love most about leading companies is designing systems to optimize how people work together. “Systems” mostly means “process”—a change in how we work to get better results. Note that “systems” does not equal “bureaucracy”—which is a type of process that reduces trust and adds transaction costs.
Every business is different, of course, but here’s a sampling of some structures my teams and I have used successfully across companies:
Personal Feedback
Weekly one-on-ones—I’ve listed this first because it’s most important. It’s an issue if you’re not meeting your manager regularly. If you lead a company, you must convey to managers that these are expected. There is no better way to provide feedback, build relationships, show you care, and catch threats before they become problems.
Feedback Week—One-on-ones will naturally veer toward project updates instead of performance feedback. So we created a monthly event called Feedback Week and asked managers and direct reports to focus the one-on-one that week on giving each other performance help. It’s a great way to break the ice.
Hourly billing reviews—In service businesses, you constantly look at billable hour numbers to manage finances, plan projects, assess hiring needs, and ensure productivity (but not burnout). So, we regularly share these numbers with managers and ask them to discuss them with their direct reports.
90-day new-hire check-ins—Every new hire needs time to get up to speed, but by three months in, it should be clear whether they are getting there…or not. Setting this up ahead of time reduces the chance of negative surprises and reminds you that it’s better to act quickly when things are not working out.
Team/Client Feedback
After-pitch debrief—Each significant client pitch or meeting must be followed by a team analysis of what worked and what didn’t. Schedule this right after the meeting, whether over airport beers or on Zoom. Open it up to group discussion and allow each person to receive input on how they performed in their piece of the pitch.
Post-campaign review—Similarly, after each major client project is complete, the team should immediately discuss how it went and what could be better next time. This is also a great time to discuss the project's profit/loss and how to share their learnings with other teams.
Quarterly client satisfaction surveys—These are still gold if you do them consistently well. Here, you’re mainly looking for complaints that didn’t surface until we asked. Even a lack of reply should be a danger sign. If they are happy and care, they will take 5 minutes to fill this out for their vendor-partner.
Mock vendor feedback sessions—When I worked at Procter & Gamble, the ability to inspire and direct creative agencies was a key part of the job. So, we had regular lunch sessions where we practiced the art of partner feedback. We could all use more run-throughs and mock training to improve in key skill areas. And it’s during lunch, so it's easy to schedule.
Company Feedback
Officevibe internal surveys—The company suggestion box got an upgrade with a tool I love called Officevibe. It sends out regular surveys to your employees and provides data and insights that you can act on immediately or monitor over time. It protects individual privacy, so the answers are more likely to be honest. As a CEO, the first messages I sought in the morning were Officevibe updates.
Best Place to Work surveys—Almost every company wins one of these awards, but few companies dig into the data. If you do look, you’ll find how your employee base compares to others, and by doing the same survey each year, you can benchmark your progress and be alerted to cultural threats.
Quarterly OGSM reviews - Objectives, Goals, Strategies, and Measures (OGSM) is the model I prefer for setting the company's business direction. These are best created as a company, with each business unit and function establishing its own. Each quarter an all-hands meeting is held for team leaders to share progress.
Annual culture offsite - Often best held in January after the silly season ends and things are just getting ramped up. Culture is the priority, and you and your teams should take on big questions like, “How are we going to keep a culture of feedback as we keep growing?” I’m happy to be available for your panel :)
The Payoff is Massive
As I hope you can see, these examples ladder up to some pretty important priorities. They are also surprisingly simple to set up. It’s mostly about establishing the process and putting some things on the calendar. The benefits are many:
You’ll see and fix the inevitable issues long before they take a toll
Issues and problems become learning opportunities
Knowing that a check-in is coming keeps performance top of mind
Managers learn what their role really is. Leaders have new ways to coach managers.
Employees, clients, and partners see that you care. That makes them want to keep working with and for you.
The biggest benefit comes from an overall culture of transparency and mutual support for improvement. You’re not just saying, “Feedback is important,” you’re doing it so much that it’s in your company's bloodstream.
Ironically, you’ll start to see more organic feedback situations happening outside the processes you add. Managers and direct reports don’t wait for Feedback Week to share how they can improve. Clients won’t wait for the survey to praise your work or bring up an issue.
We perform better in our jobs, and our employees, teams, and company grow and improve. We enjoy the business results we achieve together but mostly love improving ourselves and those around us. This is what a winning, High-Performance Organization feels like.
But it takes you, dear reader, dear leader, to take the first step in the process.
How we might work together…
Are you interested in launching your own consulting or service business or need help taking your current services business to the next level? Fleet is our holding company for services, and we’re actively looking to build business partnerships with winning leaders. Let’s talk!
My team and I lead Hearty, a boutique recruiting service that helps tech-forward companies hire proven talent. Our senior team of operators sources and screens, saving you time and money. When you need help, let’s chat.
Need help with a software project? Perhaps a product MVP, a project that requires outside help, or a fractional CTO for key strategic decisions? Our team at Shipwright Studio has worked together to build multiple successful startups, and we love helping leaders turn their dreams into reality. We're the team our clients trust for software built to last.
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Feel free to schedule a time during my Office Hours to discuss questions, feedback, networking, or any other topic!
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
Heresies of the Heart
I got a bit woo-woo in my last post, which paid off with at least one reader. My friend Nick texted me over the weekend to share how my claim that “the heart is where your real self lies” fit nicely with a post he read minutes earlier: “Heresies of the Heart.”
In this post, author Tom Morgan calls for us to seek more knowledge where our map of reality is incomplete, including the role of our heart in decision-making:
“One of the topics in most urgent need of exploration is the mysterious and neglected role of the human heart as an organ of perception and cognition. This is because if the heart has access to hidden or subtle guiding forces, it can help us navigate the world more effectively.”
Like me, Tom is another full-time businessperson who is openly curious about the world. I spent much of the weekend reading his posts, and I’m thrilled that I tipped-toed out of my comfort zone in writing about something more mystical—otherwise, Nick never would have turned me onto Tom’s work.


Like usual, good advice here. I had a manager (one you're working with again these days, I believe) who would insist after client meetings that we give each other at least one positive and one critical piece of feedback... which was sometimes tough because it was like "hey man, you were the smartest person in that room and the clients were eating up everything you said!" But it was also very good practice because as you say people hate giving feedback so getting into the habit and learning that there was an expectation to provide it helped break down some walls.
And in the spirit of "one criticism" I'll add my 2 cents that you have to be careful giving feedback immediately after a pitch. I worked for a head of an agency who we had to encourage to wait 48 hours before providing post-pitch criticisms. This leader was often focused on the pageantry around the pitch versus the content of the pitch (which was helpful at times, there are definitely clients out there who buy the sizzle, not the steak). But it was incredibly demotivating for employees who had just given up a bunch of nights and weekends to work on a pitch to hear on the ride back to the office that the CEO had a problem with the shoes they wore, or the number of times they said "um". Of course your mileage could vary on that one if you've fostered a better culture than that place had, or if you better understand the concept of a compliment sandwich!