· 9 mins · Management Skills

7 real challenges faced by managers (and how to overcome them)

Avatar of Paige Magarrey Paige Magarrey

We’ve all been there. A sticky situation comes up with your team on a Monday, and you’re still Googling random management advice by Friday, trying to parse through the fluffy “insider” tips to find actual insight from actual great leaders. 🤦

Because great leaders don’t look for Band-Aid solutions to management challenges. Great leaders go deeper into what is really going on – what emotions are driving their employees, and what perceptions might need to be adjusted.

Whether you’re a first-time manager, remote-manager or a manager of a manager, we all face similar problems and there’s a lot we can learn from one another. We want to hear from people in the trenches about the real challenges faced by managers – and what actionable advice they have for managers in the same boat.

So, we asked them.

Read on to hear about seven management challenges faced by real leaders – and how they overcame them.

1. When it feels like employees don’t work as hard as you do

At any organization, the leader will have an idea of what a good working style is. Usually, it’s their own – after all, it got them to where they are today. And when you have people on your team that don’t match your own working style, the fear (and frustration) is that they’re not working hard enough.

Chris Faller, Head of Account Development at Signpost, felt this frustration.

“I go full force eight hours a day,” he says. “Whereas I’d look at others and it seemed like they were wasting time.”

But Chris also had the insight to see past his frustration to the reality: that everyone has a different way of getting the end result. And rather than trying to get his team to adhere to his approach (an unreasonable battle that can lead to micromanagement), Chris focused on the end results – how effective his team is at achieving their goals.

“Not everyone is going to work in the same way,” he says.

By accepting their different working styles, Chris saw his employees in an entirely different light – and was able to focus on their successes as a team.

What to try: To keep your team (and yourself) focused on the results, add a weekly metrics review to your team meeting agenda. Don’t just focus on the end numbers – set weekly goals, and hold your team accountable for being on target.

2. When employees don’t want candid feedback (only praise)

If a team member seems unwilling (or unable) to take in constructive feedback, it can seem like a red flag. Are they an entitled Millennial only interested in gold stars? Are they too set in their ways to grow and improve? Should they be replaced with someone that’s not afraid of a little criticism?

But when Jill Coln of Gusto was faced with this management challenge, she looked at it from her employees’ perspective – and saw a very different situation.

“There was a fracture of trust,” she says. The problem wasn’t that her team was anti-feedback – they were insecure. Before Jill’s employees could be vulnerable with her, they needed to fortify their relationship with trust.

To build up that trust, Jill focused on connecting with her team on an emotional level. “You need to thrive on understanding their desires in life,” she says. “Truly care about what is going on in their life outside of work.”

From there, her employees felt comfortable talking with her about their weaknesses and problems – not just their triumphs.

"You need to thrive on understanding your team's desires in life. Truly care about what is going on in their life outside of work." – @jillcoln of @GustoHQ Click To Tweet

What to try: Share this video with your team to start a conversation about feedback. If it seems to resonate, start a book club to discuss Radical Candor and keep a conversation going.

3. When employees have to be told what to do, every time

You want them to figure it out on their own, but they come to you for a step-by-step plan, every single time. In fact, senior leaders spend 61% of their time solving people problems. This can be time-consuming, but it’s also worrisome long-term: why can’t my employee think for themselves?

When Greg Council, VP of Marketing and Product Management at Parascript, saw this happening with his team, he didn’t see a group of lazy workers unwilling to think creatively. He saw employees that wanted to do a great job – but were afraid of taking a misstep or prioritizing their tasks wrong.  

“They’re worried that making a mistake is career disaster. They think it’s safer to get the information directly from their manager,” he says.

So rather than simply tell his team to think for themselves or – worse – avoid their questions altogether, Greg saw an opportunity to clarify his role as their manager.

“I say, ‘My purpose here is not to provide the answers. I want to foster your ability and willingness to try to figure things out on your own.’”

Armed with that knowledge, his team can confidently start to think creatively about problem-solving – and feel safe knowing that it’s ok to take a misstep once in a while.

What to try: Make a manager README. Also known as manager user manuals, these documents outline in detail how you work, what you expect from your team and – most importantly – what your role is. Use your README to empower your team to take ownership over their decisions and feel confident about thinking creatively – even if it means a mistake once in a while.

4. When employees won’t collaborate

Your team is a sea of diverse skills and experience – so why the heck don’t your employees tap into each other’s knowledge? Are they that competitive? Do they hate working together? Do you need to get a whole new team that isn’t afraid to talk to each other?

The worst part is, that lack of collaboration can impact performance. Hilary Nalven, Director of International Carriers at Zayo Group, told us about how her sales team had a hard time relying on each other – and weren’t moving complex deals through the funnel effectively.

But Hilary saw the real issue: it wasn’t that her team wouldn’t collaborate, they didn’t know how to – or didn’t see how collaboration was critical to their success. “They didn’t know how to ask for help or pull people in,” she says.

To help them learn how to start working together, Hillary used her team meetings. “I’d ask everyone if there was something they learned or a challenge they overcame that might help the team as a whole,” she says.

Being more collaborative in meetings helped to trigger similar habits outside of them – encouraging the group to feel comfortable leaning on each other. (Ah, the power of effective team meetings 🙌)

What to try: Add a retrospective to your team meeting agenda every couple of weeks to look at what’s working – and what’s not – within the team. Include time for team members to acknowledge any help they received from each other since the last retro (at Hypercontext, we call them shout-outs!) and create a safe place to ask for support moving forward.

5. When employees don’t know they’re awesome

It’s one thing to be humble. But when an employee seems to lack self-awareness about their strengths and abilities, it can be a huge roadblock to growth.

“I want to spend time coaching them on stretch goals – not something they can already do,” says Allison Cloyd, Head of Customer Success at Maxwell.

Allison identified this management challenge as a symptom of a bigger issue: employees not having ownership over their work. She saw a direct correlation between confidence and decision-making skills – and focused on fostering the latter.

“That’s the specific trait you need to build in order to have ownership and autonomy in your team,” she says. “My team needs to feel confident about making decisions.”

Once her team built up their confidence, they felt more ownership over their work and a sense of accomplishment – and, in turn, could see their own awesomeness.

"That’s the specific trait you need to build in order to have ownership and autonomy in your team. My team needs to feel confident about making decisions." – Allison Cloyd of @ilovemaxwell Click To Tweet

What to try: Start with pep talks in your next round of one-on-ones. Tell your people that you believe in their abilities and want them to feel safe making decisions, even if they don’t always pan out. Then, add this agenda item to your team meeting: “What’s one bad decision you made this week?” Make it OK to make a bad decision once in a while – this creates a safe space for your team to gain confidence around decision-making overall.

6. When employees don’t follow through

Have you ever found yourself thinking, why did Bill spend three hours writing that blog post…but didn’t do a final proofread? Why did Susan not call that client? Why did Sal not set up that meeting?

A lack of follow-through can be a huge challenge for managers, including Ross Garrett, VP of Marketing at Cloud-Elements. “This is about taking it to 98.5%…and then choosing not to finish it,” he says.

But when Ross dug deeper into the issue, he saw things a little differently: his team wasn’t actively dropping the ball. They were lacking clear expectations around decision-making, reaching goals and asking for feedback.

It brings to mind our founder Brennan McEachran’s 1/50/99% feedback system, where you check in on projects when the work is 1% done, when it’s 50% done and when it’s 99% done – and it’s that last one that’s the trickiest. That’s when team members can shy away from asking for feedback or guidance.

“Ask!” Ross says. “Don’t let it fester.”

So, he focused on clarifying the process – what to ask for and when. And saw his team’s habits improve as a result.

“Success is about being habitually excellent,” he says.

What to try: Define “done.” This comes up a lot in agile teams: what’s the clear, concise definition of what a 100% completed project looks like? For example, here at Hypercontext things aren’t done until there’s a way to measure it. Define your “done” and then bring it into every single project your team takes on.

7. When employees seem averse to change

“That’s the way it’s always been done” – we’ve all cringed at this phrase before. Because when your team relies too much on textbook thinking, things can get stagnant really quickly.

For Teri Keller, VP of People at Sovrn Holdings, this management challenge hits close to home. Her team was small and had to wear many hats to deliver on what the company needed from them – and she had to break her team from traditional “HR textbook” way of thinking.

Any other manager might see the problem as a team too rigid and averse to change. But Teri saw things differently: a team simply focused on processes and how HR has done it in the past, rather than the full picture and value for the company.

“I want them to have the discipline to look at things from all different angles,” she says.

So, she encouraged her team to zero in less on the process and operations side of things, and take a broader look at how they could benefit the company. She was keenly aware of each team member’s strengths and development areas, and fostered an environment of learning. The unknown can be very intimidating to some, but knowing how to utilize their skills, Teri was able empower creative thinking and approaching situations from a different mindset.

What to try: Another book club suggestion: read Switch: how to change when change is hard and engage your team in a conversation about how they can feel safe changing their mindset away from their conventional routine.

Talking about all these challenges faced by managers, we’re struck by how often the initial struggle is only part of the conversation. In each of the challenges we’ve explored above, an amazing leader has gone deeper, looking to learn the emotions and motivations behind the issue itself.

It’s something that comes up again and again here at Hypercontext: the importance of humanizing the workplace. The world of work is changing, and the companies that are thriving are the ones that focus on people over processes. So, when it comes to addressing some of our biggest problems, maybe that’s the best place to start.

Easy, right? 😉

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