Leadership Challenges in the Workplace & How to Overcome Them

There’s a lot of pressure in leadership, as anyone who’s helmed a business knows perfectly well. You set the tone for everyone who works for you — what’s more, the core message of the company is yours to communicate and propagate. Provide weak leadership, and at best you’ll be ineffective — at worst, you’ll steadily shape an even weaker team.

In days gone by (days of settled employment and limited opportunities — even jobs for life), an ineffective leader of a group of independent-minded employees could just about get by in their position without being toppled or causing a mass exodus. Not so today. If you want to attract great employees and keep them around for the long term, you need to be a great leader.

Of course, being a great leader is far easier said than done, as there are plenty of obstacles in the road. To help you make solid progress, let’s take a look at some of the hardest leadership challenges in the workplace, and consider how you can overcome them:

Keeping employees healthy (physically and mentally)

People in the business world are vastly more aware of the importance of health than ever before. Not only have modern digital analytics dug deep into the operational benefits of fit employees, but there’s also been a general erosion of the stigma around mental illness (enough progress has been made that an employee suffering from anxiety is likely to be taken seriously).

As the taskmaster, your job is to get the best performance out of your team, but that’s a significant challenge because you need to get the balance right. Indulge people too much, and they’ll stop putting in as much effort — push them too hard, and you’ll cause them harm. You have to develop excellent perspicacity to tell when someone needs pushing or needs support.

Of course, another part of this challenge is setting a good example, because leaders are prone to overwork and the development of bad habits. If you won’t put in the time to protect your health, you’ll undermine all your efforts to encourage wellbeing. You have to make a priority of practicing what you preach: eat sensibly, exercise, meditate, and generally take care of yourself.

Indra Nooyi, CEO of PepsiCo (massive multinational producer of comestibles including — of course — Pepsi), put it this way: If you want to improve the organization, you have to improve yourself and the organization gets pulled up with you.” Be a shining example for your employees to follow, and they’ll find it easier to look after themselves.

Take remote working as an example. It isn’t perfect for every situation, but it’s extremely useful, and certainly something worth allowing — but if you just tell people that they can do it, they might never try, thinking that doing so would make them seem lazy. If you set a precedent of working from home by being out of the office from time to time (and letting them know that it’s a good way to work), you can let them know that it’s truly fine with you.

Trusting your employees enough to delegate

There are numerous possible reasons why you’re in charge of the team. Perhaps you founded the company, so it’s your idea. Maybe you performed better than everyone else and reached the top on that basis. Regardless, you’re confident in your abilities, and you know what you can do. Because of your responsibilities, and your position, you prefer to handle certain tasks yourself. That’s completely understandable, and not a bad idea.

However, some leaders take that sense of ownership much too far and get into the habit of taking anything vaguely important for themselves. They assign projects, then get cold feet about the possible effects and reclaim them. They ask their employees to tackle some social media tasks, then heavily rework all the content before it gets sent out. They just can’t let go.

Going about business in this way is terrible for two reasons: firstly, it steadily exhausts you through inflating your workload, and secondly, it shows your employees that you don’t trust their competence and/or character. If they work for you, they must be worth having around, so why don’t you trust them to take on some responsibilities? They might make mistakes, but making mistakes is a big component of getting better.

Tobias Lütke, head of Shopify, made an interesting note about how he approaches employee on-boarding in an interview with Bold Business: When we start new interns in our R&D team, we make sure that within their first week they actually make a change to Shopify that impacts our customers. Minutes after they send the code over, it’s going to be in front of a hundred million shoppers.

You don’t need to follow suit and give your new assistant the chance to make a change to a massive system used by hundreds of thousands of people — but you do need to identify the employees who have earned your trust and start delegating tasks.

Helping employees grow and accommodating that growth

One of the core points of hiring for the long term is that your employees will steadily develop their skills and become more valuable to the company. Someone who’s been part of your team for several years will have a lot of insight they can impart to their newer colleagues (mentoring is very important), and be capable of handling many higher-level tasks.

But a mistake that some leaders make is continuing to perceive their employees within the confines of what they’ve done so far. The only growth they consider is the inevitable march to seniority — a graphic design intern will become a junior graphic designer and then a senior graphic designer, and that’s the set path.

People are more complex than that. They have the capacity and inclination to grow and change in countless ways, and if you want to make them as useful (and as happy) as possible, you should find ways to help them grow. Are there roles they haven’t considered? Skills they might be suited to that they don’t even know exist?

In your role as a leader, you get to appraise your employees in countless ways, perhaps even seeing their strengths and weaknesses more keenly than they do. If you’re convinced that your accounting intern has what takes to be an elite-level marketer, don’t hold back from mentioning it just because you need someone working on your accounts — you can always find a replacement, and the loyalty you’ll earn through helping someone find the right career path will prove hugely valuable to your business over time.

Accordingly, be flexible in your approach. Don’t leave employees stuck in boxes just because it’s convenient. Invest time and effort into making your employees optimally effective and happy, and they’ll pay that value back tenfold.

Take Away

Overall, I’d say these are the toughest challenges faced by a modern leader. Your job is to place your trust in your employees, help them stay healthy, and nurture them both in and out of their current roles. If you can achieve that, you’ll build a team of workers who are both formidable and loyal and keep them around for the long run.

About the author

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