Leadership Challenges: 4 Common Obstacles Every Leader Must Overcome

Leadership Challenges: 4 Common Obstacles Every Leader Must Overcome

Raquel Alberdi

Feb 2, 2021

Feb 2, 2021

Feb 2, 2021

Leadership Challenges: 4 Common Obstacles Every Leader Must Overcome
Leadership Challenges: 4 Common Obstacles Every Leader Must Overcome
Leadership Challenges: 4 Common Obstacles Every Leader Must Overcome

Not long ago I remember reading a paper by the late pioneer of leadership psychology, Warren Bennis, about leadership challenges in the modern world.

In it, he discusses the 2004 U.S. presidential election between George W. Bush and John Kerry and how polarizing it was to see how one half of the country could have an entirely different notion of leadership, to the other.

The U.S. presidency has, of course, just gone through a similar “leadership crisis” with the population again taking two opposing views of what it meant to be a strong leader.

So, why was it that half the electorate perceived their candidate to embody leadership? What did they see in their head statesman that others didn’t?

While a single definition of leadership is clearly lacking (perhaps the closest we’ve come is the 5 P’s of Leadership model) which presents a challenge within itself, what are some of the other challenges of being a leader?

Let’s address some of the most common leadership challenges and how to overcome them.

Adjusting to the Role

Arguably one of the most exciting points in your career is the promotion to your first leadership role.

However, how you handle this transition period will impact your success as a leader.

Your boss has shown confidence in your ability to lead (hence the promotion/hiring) but your direct team hasn’t (yet). Some of them likely don’t know you from Adam and will require more from you than just a title before they buy-in to your philosophy.

So, you must have a plan in place to win them over.

Your best opportunity to do so is at the first staff meeting. Here you will be able to introduce yourself, demonstrate your knowledge, experience, and also address any concerns the team might have.

For example, your hiring might be the result of a strategical, structural change to the business with some roles now threatened. An obvious concern to many of your team.

Whatever the case, your team members will want to hear what you have to say.

You might fight some potential questions your team has useful in guiding your initial presentation:

  • What changes do you plan to make (if any) and how do they affect me?

  • What are the expectations from each role?

  • Is my current role secure?

  • Are you ready to get your hands dirty and help out when the going gets tough?

  • Will you be able to shield me from organizational “politics”?

  • Do you have the experience/competence to lead me?

  • Do you really know how to do my job as well as I do?

  • Will you have an open-door policy?

  • What’s your vision for the future?

Addressing these concerns, demonstrating your suitability for the role, and laying out your plans for the future lets everybody know where they stand from Day 1.

Of course, the finer details can be laid out as they relate to each role in your one-to-one sessions with team members.

But, as a rule, you’re going to want to lay the groundwork and set a strong first impression in that all-staff meeting.

Hiring and Maintaining Talent

You might have been guilty of this yourself, but when hiring for a new position, how many times have you just C&Pd the company template, changed the role a bit, added some specific job expectations, and then hit publish?

I know I have…

It’s quick, easy, and has “worked” 1000x before. So, why change it?

Well, because your hiring process could be SO much better.

Let’s take a look at a quick example.

Imagine you’re looking for a creative position (graphic designer, art director, B2B copywriter).

Do you think asking for a standard resume and cover letter, using the same monotone language found in 99% of job ads is the best way to attract talent to the position?

What creative skills are candidates demonstrating to you during this process?

None, right?

OK, so for a graphic designer you’re likely (or should be) asking for a portfolio. And yes, this will give you a fantastic insight into their work.

But to truly understand how they’ll fit into your team, why not get candidates to send in a video, solve a problem, or demonstrate their creative capabilities for the position in a manner that’s more aligned with your brand?

Hell, why not even get them directly involved in a recruitment task with your team?

This would be a much more effective method in assessing their fit for the role.

A great example of a company that’s nailed its hiring process is the web analytics tool, Hotjar.

On their career’s page, you’ll find a clear, transparent overview of their 5-stage recruitment process:

Our five stage recruitment process

Each stage is designed to test a candidate’s suitability against several different criteria. The process culminates with a 2-week (paid) task where candidates are encouraged (well, required) to communicate and work with internal staff.

While it might take a month or two from start to finish, by the end of the process, only the
best-fitting candidates remain.

I bring this up because, as a leader, your primary role is to get the most out of your team. So if it’s made up of highly-talented, motivated, and suitable individuals, then half the leadership battle has already been won.

Making sure you hire (and retain) the right people will go a long way in ensuring your leadership tenure is a success.

Implementing Changes

“Uh oh, here we go again…”

How many times have these words run through your head every time management announces a new initiative, organizational restructuring, or shift in business strategy?


To many employees, these changes seem like just another fad or the latest idea to pop into the CEO’s head.

“I went to a marketing conference and read about a case study of how an unrelated company made millions by implementing “X” strategy.”


“I’ve been reading a lot recently about “Y” buzzword and am concerned we’re not doing anything about it…”

These are not compelling reasons for staff to get on board.

For it to work, employees need to understand the purpose behind these changes, and why now? What is the expected value to be gained, and do we buy into it?

As a leader, you must communicate to your team that this is NOT just another fad or spin on the CEO’s Ferris wheel.

Be transparent. Show them the long-term implications of this change and how they, individually, have a vital role to play in the initiative.

Your job would be made even easier if these changes align with the company’s core values. People are a lot more inclined to buy-in to new initiatives if they can see the larger picture.

As you’re aware, people need time to adjust between structural or strategic changes. They very rarely overlap and cause a great deal of confusion, resentment, and drop in morale if not handled with care...

So keep that in mind.


As I mentioned previously:

“The primary role of a leader is to get the most out of their team”

It would make sense then that evaluating their performance, developing their skills, and highlighting areas for improvement be a key area of leadership.

Now, there have been many books written about feedback delivery. But for me, the most effective I’ve come across is Kevin Eikenberry’s Four Type Model:

Negative feedback: corrective comments about past behavior (things they didn’t do so well).
Positive feedback: affirming comments about past behavior (behavior you’d like to see repeated in the future).
Negative feedforward: corrective comments about future behavior (things that shouldn’t be repeated in the future).
Positive feedforward: affirming comments about future behavior (things that would improve future performance).

So, why do I like this approach to feedback so much?

I think it strikes the perfect balance between both “carrot” and “stick” with an emphasis on how individuals can improve in the future.

When conducting a feedback session with a team member, it should always be done in a back-and-forth questioning format.

Not an interrogation, but an opportunity for them to dig down and get their assessment.

You’ll want to ask questions about all four types of feedback. For example:

  • How do you think “X” task went?

  • Specifically, what do you think went well?

  • What do you think could have been improved?

  • Knowing that, what would you change/do differently next time?

  • Are there any processes/actions you think can be avoided?

This exercise is about getting your team to connect the dots themselves. It helps move the conversation away from a defense of their past actions (which can’t be changed) towards a renewed focus and eye to the future.

Are You Ready to Overcome These Leadership Challenges?

I hope that after reading through the four most common leadership challenges, we’ve given you enough actionable advice to identify and overcome these obstacles.

However, there are of course dozens, if not more issues leaders face daily. We’re keenly aware of that.

So, if there’s a particular leadership challenge you’re facing outside of this list, we want to hear from you. Let us know in the comments below what it is, how it pertains to your particular situation, and we’d be more than happy to help.

Thanks for reading!