Your Startup’s Management Training Probably Sucks — Here’s How to Make it Better

Your Startup’s Management Training Probably Sucks — Here’s How to Make it Better

Plenty of startups leave manager training on the backburner until they become a bigger company — or try to fit it into a 30-minute lunch-and-learn. Melissa and Johnathan Nightingale, founders of Raw Signal Group, unpack why this is a mistake and outline their top tips for management training.

SO, WHEN DO YOU NEED TO START THINKING ABOUT MANAGER TRAINING?

Johnathan and Melissa point to a few key phrases that they often hear from founders that indicate it’s time to start making manager training more of a priority. “For venture-backed startups, it’s always a flag when we hear early-stage founders saying: ‘We’ve doubled in size, but we haven’t doubled our output. It feels like we’re going slower,” says Melissa.

When you’re a really small startup, co-founder drama is the likely company-killer. But as your org gets larger, the thing that often tanks the company is waiting too long to bring on competent management.

When talking to founders for the first time, Melissa leans on a simple assessment question: ‘How big is your organization today, and what size are you planning to be by the end of the year?’ The planned growth trajectory tells you so much about what struggles are likely to crop up in the organization,” she says.

The Raw Signal crew also points to a few general milestones that most often cause founders to pick up the phone and ask for help with management training:

Founders — look for canaries in the coal mines.

As a startup grows, the founding team becomes one step (or a few steps) removed from the chaos of the day-to-day. The Raw Signal team advises folks to lean on both qualitative and quantitative data. “HR leads tend to have a clear idea of what’s going on in different parts of the organization, and where there’s friction. Sometimes it could be Finance leads. You’re looking for leaders who are working with a bunch of different parts of the organization at any given moment — they have the pulse on where things are smooth, and where they aren’t smooth,” says Melissa.

That said, repeat founders have a leg up here. “Serial entrepreneurs tend to come to management training much earlier. They often have stories from their last company, and are more acutely aware of the impact of training leaders and managers within the organization sooner,” says Melissa.

7 MANAGEMENT TRAINING MISTAKES YOU MUST AVOID.

“When we first founded Raw Signal Group, there was very little training out there. I believed that any training was better than nothing. Orgs that had some training in place (no matter what it was) were better off than those that took a ‘throw them in the deep end’ approach to management,” says Melissa. “But over the past five years, we’ve seen a lot of programs that were actually worse than nothing, turning participants off of management completely because they’re so poorly run. If you aren’t thoughtful about how you build and execute these programs, you can end up making a giant mess of things.”

As an example, the Raw Signal folks had worked with a company with a deeply-technical workforce that had previously done some very corporate, dry management training. “It was a complete failure. Leaders were frustrated that most folks failed to even complete the mandatory training. It had gone so badly that the company declared a hiatus on the training while they regrouped,” says Melissa. “To combat this, when we rolled out new training, we made it entirely optional. Understanding that managers were uncertain about the value of training and giving them space to warm up to it made a massive shift in how the program was received. After our first cohort of opt-in manager trainees, the word of mouth buzz got other folks excited to attend.”
The good news? Folks want to get better, given the right tools. “The experience of being an untrained manager is so hard. It’s stressful to show up every day and not know how to answer the questions from your directs. Or to know you have feedback for your people, but don’t know how to frame it,” says Johnathan. “When you give those people actual skills, you don’t have to push them very hard to use them — it’s water in the desert. You’re able to give directs feedback in a way that’s not going to blow up your management relationship, but instead, they will receive the feedback and get better from it.”

1. Trying to build training in-house.

While first principles thinking can give startups an edge, creating manager training from scratch is often not a worthwhile endeavor.

“If you’re not planning to be the best in the world at some system, you don’t tend to build your own. It’s why startups use somebody else’s payment provider or someone else’s CRM,” says Johnathan. “But we meet small startups who decide to develop all of it in-house because management is very close to their own culture. Sooner or later they realize that there’s so much content to cover and they have to build out an entire learning and development team to create a custom program.” Alternatively, many founders toss the ball over to the HR department. “Many founders think, surely this is an HR issue. So they ask HR to put together a presentation on building a feedback culture or doing 1:1s. But many of the people who are skeptical of manager training to begin with are skeptical of HR as a function,” says Melissa. “It’s very easy to say, ‘I’m an engineering leader or a sales leader. What HR has put together sounds great based on HR, but that person has never led engineering or sales.’ So they choose to ignore all of the things shared in the presentation because they don’t think it applies to them.”

2. Only training new managers.

For orgs that have already implemented some degree of leadership training, the Raw Signal folks see plenty that roll out training just for new managers. “This leaves the entire mid-senior and exec layers under-equipped,” says Johnathan.

He points to a few friction points:

3. Siloing manager training by department.

Similar to siloing leadership training just for new managers, Johnathan and Melissa see these programs stumble at the starting line when it’s designated for particular departments in the org. “A common mindset is that manager training is all about helping managers work better 1:1 with their reports. But effective management training is about the entire org,” she says.

For example, training sales and engineering leaders separately. “Guess what happens when those leaders try to work cross-functionally? They talk past each other and have wildly different expectations. If your org is already siloed, separate manager training makes it worse. If your org isn’t siloed yet but you train leaders by department, watch how quickly silos form,” says Melissa. “Training should reflect the realities within the org. If eng is never expected to collaborate with sales, ok. But in most startups, the overlap of departments is where things fall apart. Management training should bolster those relationships.”

4. Snacks are good for the kitchen. They’re less useful for leadership lessons.

With jam-packed schedules at a fast-growing startup, folks are often looking for the “Minimum Viable Training” option — the smallest, snackable option with the least intrusion on leaders’ day-to-day. “We often hear: ‘Can we fit it in a lunch-and-learn? How small can we crunch down the nugget of information so it doesn’t interrupt the ‘real work’ we need our managers to do?’” says Johnathan.

The MVT approach misses on several fronts. “First, it signals to leaders that the org doesn’t value effective management. Second, it doesn’t provide enough room to dive into the why behind best practices. If you’re trying to implement a new behavior, I need to understand why it matters and how to tell if it’s working. Deeply technical teams understand that without the why, they won’t do their best work,” says Johnathan.

He sketches out an example: “There’s a lot of training out there that’s very prescriptive: You must do weekly 1:1s, they must be 30 minutes, and the manager must set the agenda. Or, you must do quarterly OKRs. But people don’t leave with an understanding about what’s behind those ‘musts,’” says Johnathan. To leave more space to dive into the why, the Raw Signal Group founders typically work with management teams across six weeks, meeting on a weekly basis.

5. CEOs want to join in.

The Raw Signal co-founders have seen plenty of CEOs with good intentions join in on manager training — to the detriment of the program. “Founders often come from a place of, ‘Yes I’m the founder, but I’m part of the team too.’ We love the humble energy, but we’ve never seen a team where the CEO or founders joining didn’t change the dynamic in the room. Even the most approachable and accessible CEOs alter the vibe,” says Melissa. “If you want leaders to do the hard work and bring honest, vulnerable questions to the training sessions, you need to design for that upfront. That starts with being clear-eyed about how power exists within the organization.”

6. Horoscopes ≠ skills development.

In the past decade, there’s a multitude of personality assessments that have cropped up — you’ve probably taken at least one of them, including DISC, Myers-Briggs, Strengths Finder, and Enneagrams. “Many folks say these tools have opened up new understandings of themselves, and we’re generally fans of any tool that helps leaders reckon with how they’re showing up at work and identify areas of strength and weakness in their own leadership,” says Johnathan.

The problem lies when these tools for internal self-discovery are turned outwards towards team dynamics. Here’s why: “When I use a tool to learn about myself, I jump to the parts that I feel are really unlocking something important about who I am. The pieces that don’t resonate I will ignore. But when I apply those same traits to someone else, I don’t have that deep knowledge to throw out the pieces that don’t quite fit. The tool makes others into shallow caricatures, instead of fully-realized people,” says Johnathan. “There are 16 Myers-Briggs types, four letters in DISC, and 9 Enneagram numbers. Trying to force-fit a team or a whole company into a framework like that oversimplifies things.”

If you’re a fan of any of these frameworks, there’s no need to throw them out entirely. “A training that employs any of these tools as a component of self-discovery is one thing. But training that’s anchored entirely on one of these tools is going to frustrate the participants when they leave the training session and try to put it into practice,” he says.

7. People hate role-playing — and it generally misses the mark.

It’s possibly the most dreaded part of any leadership training — grab a partner and act out a scenario that demonstrates something you’ve just learned, like how to give difficult feedback to a direct report. In addition to being just plain awkward, the Raw Signal founders don’t find role-playing to be of much use. “Programs that use falsified constructs are difficult to apply when I’m back in my day-to-day context. It’s hard to deliver tough feedback to real humans. Delivering it to imaginary humans is designed to make it easier. But when I’m back in front of a real human, the things that were difficult are back again,” says Melissa.

Instead, the duo advises creating a space where managers feel safe talking about the actual struggles they’re having. “Whether it’s my own struggles or a peer’s, hearing them talk about it in real terms, and seeing how different tools or perspectives clarify things, is far more powerful and lasting,” she says.

Here are their tips for session facilitators looking to create the space for vulnerability:

THE 4 TOPICS EVERY MANAGER TRAINING SHOULD INCLUDE.

Whether you’re working with an outside firm or tasked with creating your own leadership training, the Raw Signal founders suggest that all training covers at least four particular modules. A few of these topics may not sound like things you’ve covered in past lackluster management training sessions, but they’re key to laying the foundation for fast-growing startups.

Across each module, the goal is to ground folks in their past experience as a direct report — even if they’re many years and titles removed from that more junior part of the org. “As you get more senior in the organization, it can be really easy to lose touch with what it felt like to not have much power. Or what it felt like to have a boss who’s constantly changing their minds. Or to have a boss who was mostly unavailable,” says Melissa. “So when we work with leaders, the starting point is to talk through experiences from their own careers. That way, when we talk about the actual skills, they’re grounded in why it matters and why this is work worth doing well.”

WRAPPING UP: REMEMBER, MANAGEMENT IS A TOTALLY DIFFERENT ROLE.

“One of the most disorienting things about stepping into management for the first time is that no matter how much you want it to be the same as IC life, it isn’t. Not the work you’re expected to do, or the problems you’re solving, or even how your calendar looks,” says Melissa. “While many folks know intellectually that management is different than individual contribution, most first-time managers are unprepared for how much changes so quickly.”

In terms of easing the transition, the Raw Signal folks hope to tweak the initial message. “I’d love if every time we promoted someone to management, we said, ‘Congratulations, we’re excited about this next step. But I want to be crystal clear — this is a different role than what you were doing before. The things that made you successful in your past role are still relevant, but the things that will make you successful in this new role are different. They’re learnable, but it’s going to take some work,’” says Melissa.