Accelerating Your Product Team through Workshops
As a leader of product managers, one underinvested lever for growing your product’s revenue and profits is to strengthen the skills of your product team.
Too often, product leaders don’t invest enough organizational resources into honing the skills of their product managers. Why is that the case?
In this essay, we’ll first illustrate why this problem arises in fast-growing product organizations. We’ll then discuss how professional development workshops can solve this problem for product leaders, and we’ll wrap up by providing a guide for how to assess workshop providers.
The challenges that fast-growing product teams will face
Let’s step into the shoes of a fictional product leader who has successfully shepherded their company through multiple stages of maturity.
As a product leader, your objective is to accelerate the growth of your company. Much of the time, that means focusing on vision, strategy, and mission. It means identifying what markets to attack next and which big bets to make. Most of your time is spent on business strategy.
During your tenure as a product leader, you’ve taken the company through multiple rounds of fundraising, and you’ve enabled the company to establish a presence in new markets. Colleagues throughout the company have deep confidence in your abilities.
In theory, all should be running smoothly. You and your product management team have a demonstrated track record of success. Your product portfolio has won accolades and press releases, and the positive customer testimonials have been pouring in.
Yet, over time, the skills of your product management team will drift away from the evolving needs of your customers and your cross-functional counterparts.
Skills/market fit drift is a natural phenomenon, and it happens so slowly that it can be hard to notice until it’s too late.
The root cause of PM team skills/market mismatch
What causes this skills/market loss of fit?
As your company experiences hypergrowth, the skills that your product organization needs will change because you’re tackling new markets and new problem areas.
But, without investing sustained effort into your individual contributor product managers, you’ll find that their skills will no longer meet the new needs of your customers and your company.
To clarify, you can trust your IC PMs to grow new skills on-the-job on an individual basis. But, without an overarching skills development plan, you have no way to ensure that the skills mix of your product team will naturally line up with the changing needs of the various markets that you’re tackling.
On top of that, because the company has grown so quickly, you’ve also grown the team by 2-5x in product manager headcount. When you quickly bring in lots of new talent, but don’t have onboarding programs in place yet, these talented people will naturally have different processes and decision-making frameworks.
While these processes and frameworks are valid in specific contexts, they may not mesh well with the specific context of your particular area of focus. This causes new product launches to have a higher risk of failure, and causes your product scaling initiatives to move less quickly and to achieve less-than-optimal results.
The downstream impacts of skills/market loss of fit
As more and more initiatives start to show signs of weakness, your cross-functional departments start to lose trust in the product team. What used to work at an earlier stage of the company no longer works at the new scale in which you operate.
As a product leader, you know that you need to intervene. You consider personally leading professional development initiatives for your individual contributor PMs. But, the problem is that you’ve got so many things to tackle right now that it’s not the best use of your time for you to personally train them.
So, you reach out to your people managers - VPs of Product and Directors of Product - and ask them to upskill their teams.
But, your people managers have the same problems that you have. They need to run their own product portfolios, and they can’t sacrifice the time to directly train their PMs in the craft of product management.
The most they can commit to is regular 1:1 sessions with their direct reports. But, these 1:1 sessions don’t solve the broader macro-level problem, where the portfolio of PM skills doesn’t align with the company’s portfolio of problem areas.
So far, you’ve considered training the product team yourself, and you’ve also tried to get your people managers to train the product team. Neither approach seems to work. But, what about asking senior IC PMs to train the product team? Surely they have more time on their hands?
You reach out to your most senior IC product managers to ask whether they have the bandwidth to train their peers. But, the response you get back is the same from each one of them. They’re focused on leading their individual focus areas, and so at most they can only handle 2-3 mentees at once. They can’t commit to training the entire product team.
Their response makes sense to you. After all, their formal job is to keep moving their product forward. You can’t ask them to pivot away from their day-to-day work, because they’re leading the highest-visibility, highest-impact, highest-risk initiatives at the company.
Over time, the skills/market gap widens within the product organization. To try to fill the gap, everyone on your team is hustling as hard as they can.
Each quarter, you find that people are working longer hours than the quarter before. They’re all executing more and pushing themselves to do more to lean into the skills/market fit gap.
But the problem with this approach is that execution doesn’t fix the gap. While no one has the time to invest in team-wide foundations, not investing in foundations is an even costlier mistake. Worse, you’re starting to hear reports that your product managers are experiencing burnout, and that teammates are no longer deeply convicted that your product team is the right place for their long-term careers.
Attempting an internal-only turnaround
To combat burnout, some of your more dedicated product managers try to implement team-wide processes, whether it’s “how to release” or “how to write a spec” or “how to run a bug bash.” Yet, when they run these internal trainings, less than 20% of your PMs show up because they’re too busy with work. Your processes continue to fracture.
To stop the bleeding, you announce changes to the product process in your next product team all-hands meeting, in the hopes of standardizing processes across your product team. Yet, your announcement mostly goes unheeded because everyone’s too busy executing. After a few attempts, you silently stop pushing on this thread of “standardizing the product process.”
In reflecting on the skills that your product organization is missing, you decide not to train from within, because it’s an uphill battle that takes too long to pay off.
You instead open up multiple job opportunities for senior product managers. Your thought process is that if you can bring in senior product managers who have the skills that your organization needs, then your team will no longer have a skills/market mismatch.
But, there’s a supply and demand problem with this approach. Many other fast-growing product organizations have run into the same problem that you have, and they’ve also decided to hire senior PMs. Because everyone’s hiring senior product managers, there aren’t enough to go around, and your job openings go unfilled for months at a time.
In the meantime, your product organization continues to soldier on with its fractured processes and with a vacuum of organizational development.
Over time, this leads to attrition from your individual contributor product managers - they’re ambitious and they want to learn on the job, but they’re frustrated that the organization hasn’t invested in the growth of their skill sets. They find opportunities elsewhere, at product organizations that are more committed to their professional development and growth.
You know firsthand that replacing a product manager doesn’t come cheap. You have to source candidates, interview them, and onboard them. You know the cold hard numbers: replacing a highly-trained employee costs 150-250% of their annual salary.
Positive testimonials from customers have started turning into frustrated escalations. The company starts to miss its quarterly earnings targets. The product portfolio feels much less manageable than it used to be.
You’re exhausted. You’ve tried all that you could, but the skills/market gap continues to widen. You’re not quite sure where to go from here.
Well, you don’t have to go it alone.
You can bring in people who are dedicated solely to teaching the craft of product management, even if they’re not full-time employees or individual contributors. In other words, rather than trying to build the capability of “PM development” in-house, you can delegate it to dedicated specialists instead.
Solving the skill/market drift problem
As more and more product organizations reach significant scale, enlightened product leaders understand the need to reinvest in fundamentals, and understandably don’t want to burden themselves or their teams with the hard work of curriculum development or ongoing training.
That’s where workshop providers come in. Live workshops provide live synchronous training, eliminating the problem where only a few product managers show up to informal “lunch and learn” sessions.
Because the entire team is there, everyone can clarify their questions and arrive at a joint understanding. In other words, a live workshop is far more valuable than announcements or asynchronous process documents, because workshops give every product manager the ability to calibrate themselves with their peers.
With team exercises as part of workshops, your product managers will have the opportunity to break down the silos between them, to build up rapport with one another, and to experience best practices in action.
By leveraging workshop providers, you no longer need to allocate precious senior talent to the continued skills growth of your product team. You can focus more on identifying “which new skills do we need” and “what processes do we need to standardize”, and workshop providers can take care of the rest.
As for the curricula and structure of the workshop, you can elect to use “out of the box” workshops with a predefined curriculum, or you can leverage “custom commissioned” workshops where you craft your own targeted curricula in partnership with an expert practitioner.
You can get your specific organization’s needs met through these providers. But, how exactly do you select the right provider?
How to assess product management workshop providers
To assess product management workshop providers, conduct the following due diligence:
Check if they’ve done workshops before
Ask if they’re open to free consultation with you
Review their past publications, such as books, essays, speaker events, and videos
Verify their track record in shipping their own products
First, you’ll want to ensure that the provider you select has run workshops before with product organizations. That is, some product coaches may be great with 1:1 sessions, but they may not have a track record with larger group settings yet.
As an example, check out Product Teacher’s work with one of its clients, Convergence.Tech. In this workshop case study, we share how we enabled a diverse team of product talent to gain new skills and approaches.
Second, see if the provider is open to a free consultation with you. Live conversations will help you better understand their particular strengths and their existing offerings, and will also give them a chance to better understand your needs and focus areas.
Third, check to see if your provider has any past publications. Ideally, they’ll have published product management books and essays before, because that demonstrates that they know how to structure their thoughts at scale.
And, ideally, they’ll also have conducted speaker events and recorded videos before, because that proves that they know how to interact with live audiences in a synchronous way.
Finally, check to see that your provider has had prior product management experience themselves. If you’re looking to ship multimillion dollar products, you should use trainers who have also shipped multimillion dollar products. If you’re trying to break into new markets, you should use trainers who broke into new markets during their time as individual contributor PMs.
By conducting this due diligence, you can ensure that you’ve selected a provider who can grow the skills portfolio of your product team. That then eliminates skills/market mismatches, standardizes processes within your organization, creates trust with your cross-functional counterparts, drives positive customer outcomes, and increases your ability to retain talent.
Closing thoughts
You don’t have to go it alone as a product leader.
Every leader knows the build vs. buy analysis when it comes to product functionality. You build for the highest ROI cases where your ownership is irreplaceable, and you buy to open up more opportunities for building. You know that you can’t build everything, or else you’ll experience sharply decreasing marginal returns.
But, few leaders use the build vs. buy analysis mindset on professional development. Many leaders fall for the trap of “needing to build their own professional development programs,” which winds up draining their teams and leading to less-than-optimal results.
As a product leader, by focusing on the business and by delegating training to a workshop provider, you can strengthen the foundations of your product team, enabling you to achieve both short-term “wow” results and long-term sustained market leadership.
