The 2 Most Difficult Management Challenges To Overcome

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One of the mental changes we all have to make when we become managers is that we often lose the satisfaction and gratification of doing work that makes an immediate impact.

We don’t spend all our time shipping code, designing features, launching marketing campaigns, or presenting reports — all things that tangibly delight customers and our colleagues. If we still do, we’re doing it wrong.

Instead, we spend time advising, building trust, mentoring, coaching, delegating, coaxing, contextualizing, meeting, and coordinating.

The impact of this — teams of happy, diverse employees delivering sustained high performance — is remarkable. But that impact isn’t felt every day.

Sometimes, it can feel like you’re not having much impact at all.

You may be lucky enough to have management cheerleaders within your organization who will remind you that your role is arguably the most important (and undervalued) at the company. But articulating exactly why that’s the case isn’t easy.

You can help create a career and workplace that will dramatically impact someone’s life to the extent that they’ll tell those closest to them about what you’ve done for them.

Not many other colleagues get to say that.

How Management Challenges Impact You

You have plenty of management challenges that don’t exactly lend themselves to clear goals or answers, but two stand out as particularly cumbersome: managing employee expectations and managing underperformance.

The problem with these two particular issues is they significantly impact nearly every aspect of your employees’ working lives: professional development opportunities, positive work environments, goal-setting, employee engagement, team productivity, personal well-being, and more. You’re the catalyst for improved company culture and a contributor to making work enjoyable for everyone.

Counterintuitively, the biggest challenges don’t always require the biggest solutions, yet your management skill set can only take you so far. While effective communication, decision-making, and time management are integral, these outlying management challenges require a certain panache and attention to detail.

Use these ideas and a combination of your innate skills to overcome these management challenges.

Management Challenge #1: Managing Employee Expectations

A panicked woman looking at her laptop

If managing underperformance is one of the greatest challenges for first-time managers, then dealing with unrealistic expectations might be its frustrating younger cousin. Sometimes, pinning the problem down is almost a fool’s errand.  

Underperformance is often due to a specific behavior you can point to and work on. For example, internal communication isn’t good enough, which means we’re missing deadlines. Analysis quality isn’t sharp enough, so clients aren’t getting value from our products. These are things you can try to fix.

However, “I’m unhappy because this job isn’t what I thought it would be” is a much harder issue to tackle.  

It can also translate into disgruntled team members trying to drag otherwise happy colleagues into their well of disappointment. Things can get pretty toxic, and often, by that point, it’s too late.

Managing Employee Expectations on the Fly

This is one of the lessons from the latest blog post by Katie Wilde, a VP of Engineering at Buffer. In it, she reflects on where misaligned expectations between her and certain team members about their roles led to toxic situations and, ultimately, resignations.

She pinpoints four areas where you can work to get on the same page:

1. Recruiting and Hiring

Recruiting and hiring are your first opportunities to set expectations. Yes, you want to promote your company and attract talent, but you also want to make sure you’re not over-selling, particularly in areas where there might be friction. Wilde says she asks what frustrates people at work, and if some of those dynamics exist at Buffer, she’s open about it so the candidate can make an informed decision if that’s a deal-breaker for them.

2. Onboarding

If you want to help a team member successfully navigate your organization, you’ll need to tell them about messy parts and the workarounds people use to get stuff done. Onboarding is a good time to do this. For example, Wilde says she’s been open with new hires about a reorganization that’s going on and how to work through that.

3. Setting Boundaries

Letting people know what behaviors are and aren’t appropriate on your team can be difficult and could take up a whole post on its own. You shouldn’t have too many of these conversations if you've hired well. But you may have to intervene if you see something that’s not OK. Wilde uses the example of a team member constantly using team meetings to publicly vent her issues. In these instances, timely feedback to set boundaries is essential.

4. Teaching Disagree and Commit

Teaching “disagree and commit”: As a manager, you won’t always solve every problem for every team member or agree with them on every issue. You have multiple team members’ interests to balance with those of your company. That’s a management challenge in itself.

When an issue is beyond your control, or you’ve prioritized someone or something else over a team member, you need to be clear about it, explain why, and ask them to commit to moving forward. If they can’t, consider whether the team or company is the right fit for them. Continually disappointing someone by failing to solve issues beyond your control or letting those issues fester is a recipe for disaster.

Management Challenge #2: Managing Underperformance

A man in a tie and glasses holding his hands on his head in frustration

In our conversations with new managers, one of the most common challenges we hear about is helping an underperforming team member.

To exacerbate the situation, it can be difficult to get good advice on this subject. The topic covers such a wide range of situations — different personalities, different sectors, different working relationships — that we find much of the guidance out there is too general to be of much practical use.  

That was until we found this blog post from Roy Rapoport, a Director in Corporate Engineering at Netflix. He lays out “The Five Conditions for Improvement,” which need to be in place for you to help someone work on an aspect of their performance.  

This checklist is an invaluable resource for working through these issues with your team members:

  1. Does your team member agree there’s a problem? If they don’t think there’s an issue, you’re not going to have much success convincing them to solve it. Start here.
  1. Does your team member want to see the problem resolved? They might be aware of the issue, but they might be fine with it. You’ll need to help them see why it’s important to resolve if you want to make any progress without micromanaging the situation.
  1. Does your team member see their role in causing the problem? Ah, so they might recognize a problem exists and that it needs resolving but don’t see how it’s their issue.  Again, no point going any further until you have an agreement that it’s something they’re impacting.
  1. Can your team member figure out a plan to solve the problem? OK, we’re making progress. They’ve agreed the problem exists, needs resolving, and they need to take action. They just might not know how. This is where you might need to step in and offer some advice in a personalized or one-on-one setting.
  1. Can your team member execute the plan? Even if they have a plan, can they actually make the relevant improvements? Again, as their manager, this is where you can offer support.

We’ve seen many cases of underperformance in which a manager has simply skipped points 1 through 3. They’ve given the individual some instruction to improve without ever pausing to consider whether they believe there’s a problem in the first place, care about it, or think it has anything to do with them. This is clearly a recipe for disaster and happens — well — it happens all the time.

Next time you need to speak to someone about improving, spend a few minutes thinking about whether these conditions exist. If you’re currently struggling with one of these situations, check the list to see if you’ve missed a step.

Solutions To Management Challenges That Build High-Performing Teams

A man with glasses wearing a button-up smiling at the camera

One of the hardest questions and management challenges we face as leaders is whether we’re actually doing a good job. Rarely do employees or executives go out of their way to acknowledge the challenges managers face and how they’ve overcome them.

Sometimes, you haven’t overcome the challenges at all, and you’re waiting for some sign to push you to the next step. But that’s not going to happen.

Proactive approaches are the only way to solve management challenges in both onsite and remote work. If you’re desperately searching for solutions, add these to your skill set.

Be Comfortable Showing Emotions

Expectedly, higher-performing teams communicated more often than others, and the types of communication were more interesting. These teams are more comfortable expressing positive and negative emotions to their teammates. They’re more likely to tell jokes and tease their colleagues, but also to use sarcasm, complain, and curse with each other.

So, should you swear more in meetings to raise performance? Probably not. But it's more about getting your team to a point where they know each other well enough that they're comfortable expressing themselves honestly with one another. You’re the catalyst for that.

Frequently Share Appreciation

People on high-performing teams received nearly twice as much appreciation from their teammates and twice as much from their managers than those on other teams. There’s no coincidence that praise is inherently linked to appreciation.

Work Hard But Maintain Balance

High-performing teams agree that their teammates pull their weight. However, they also believe that their teammates value work-life balance. As such, the win-at-all-costs mentality acts as a burden to workflow. The true solution to the management challenge of getting results is working hard yet respecting each others’ boundaries.

Have More Social Activities

High-performing teams are more likely to engage in a variety of non-work activities. They grab tea or coffee more often, go to happy hours, and even discuss books together.  Does this conclusively prove going to the bar raises team performance? Not always. But when you can schedule a friendly check-in that encourages socializing, you’re on the path to success.

Provide Clarity on How Your Team Can Contribute

The best teams have more clarity on three vectors: how their work relates to their team’s goals, how their team’s work aligns with their company’s mission, and how their company contributed to making the world a better place.

Clarity is the glue that holds your team together and provides a vision for common goals, but it doesn’t come with a template. You need to actively provide this information to reach goals and milestones. The more upfront and transparent you are, the better.

Get By With a Little Help From Your Friends

Management challenges arise from new situations, hires, and conflict. It’s how you resolve these situations that can pave your way to becoming a great leader.

Unicorn Labs understands the challenges you face as a manager. We thrive on these situations and the opportunities to learn along the way. We also know that not every manager is given the tools to circumvent management challenges.

That’s why we have leadership coaching, online courses, and retreats — all designed to improve your leadership and management skills, as well as the skills of those around you.

Schedule a call today to learn how Unicorn Labs can provide the perfect solution to your management challenges.

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