The Biggest Challenges Leaders Face in 2021

We all know that 2020 was a challenging year, but the challenges didn’t stop just because the clock struck midnight, the ball dropped, and we entered a new calendar year. Challenges are a part of life and we’ll have our share of challenges in 2021 too.

The word “challenge” tends to have a negative connotation. And while I’m no optimist (realist right here!), I see challenges as problems that need to be solved, struggles that need to be overcome, and a whole lot of opportunity to grow as a person, business owner, and leader.

So, I for one, welcome the challenges that leaders are going to face this year. Let’s hit them head on and get ahead of our competition. Challenges are where the pros show up and where great companies start to separate from the pack.

In 2021, the biggest challenges leaders are going to face are challenges that stand the test of time. They are the same challenges that companies have every year – time, money, and people. Let’s dive in and see how those timeless challenges show up, what unique problems 2021 may bring, and most importantly how to navigate through these challenges to get ready for a banner year.


Everyone has the same 24 hours in a day, so why are some people more successful than others? It’s because they understand the importance of saying no. They understand that not everything matters equally. And they understand how to hold their team members (and themselves) to high standards of productivity. We’re always racing against the clock – that challenge is never going to go away. What you do with the time that you have is where you can get a competitive edge.

2021, especially in the first half of the year, is going to present us with many of the same challenges we faced in 2020 – from homeschooling, to work from home partners, to home renovations (with increased costs and delayed timelines), and staying up to date on the rapidly changing market, economy, and rules and regulations. Not to mention there will likely be even more technological advances to how we work, which brings its own set of challenges to learn and implement these tools. And with every new piece of technology – product or service – there comes sales pitches and demo videos competing for our time and attention.

So what do we do when we’re being hit from every angle with demands on our time from our team, our clients, our family, vendors, the media, and more?

We slow down and get clear. The best way to know how to allocate your time is by getting clear on what is most important to you, your team, and to the growth and success of your company, career, and life. While your ideal schedule in 2021 may not look exactly ideal anymore (due to issues outside of your control – homeschooling, your partner’s work schedule, etc.), keep the most important things top of mind. If working out, having dinner together as a family, networking for 2 hours, and holding a team training every day are the most important activities, then everything else needs to be scheduled or rescheduled around those things. Make them non-negotiable and share those priorities with your team and clients. Clearly setting expectations around your time and priorities helps others to do the same.

Remember, not everything matters equally. With increased demands on our time and endless Zoom meetings, go back to your list of most important daily activities and say no to everything else.


The biggest challenges I see leaders face with money comes down to making poor investment choices and not holding their money accountable. Let me explain.

When entrepreneurs and leaders are growing a company or division, it’s tempting to live beyond their means, or even at the edge of their means, and take all or the majority of the profits from the business. Especially if the business is booming (in 2020, that included the real estate industry, big tech, streaming services, food delivery services, online retailers, and more). The challenge when there is profit is NOT to spend it. Difficult, but doable. Now is the time to double-down on cutting expenses, re-negotiating contracts, and extracting as much money as possible from the business and putting it into reserves.

Now, I say this, but there is a caveat. Knowing when to pull the trigger and invest is important too. Wading  through all the shiny objects (i.e. new tech tools that promise you’ll close 100 more clients a year), merger and acquisition opportunities, and even legitimate operational systems or new hire decisions are their own unique challenge. As many of these industries continue to hold strong in 2021, it will be challenging to decide when and where to invest, and when to scale back, cut expenses, and build up that reserve account.

I’ve always run a lean business model and believe in leading with revenue. So where do I choose to invest? People. People, the right people, will always give you a return on your investment.

It’s not enough to just invest your money wisely, leaders also need to hold that money accountable. Can you honestly say that you, your Force Multiplier and/or your financial team are paying attention to where every dollar goes and whether or not you are receiving a return on that deployment of cash? If not, then it’s time to review where your money is going and make adjustments. This could mean cutting expenses. This could also mean increasing ad spend on your most valuable lead generation source or giving a raise to a team member who has gone above and beyond over the past six months.

If this year taught us anything, it’s that we never really know what can happen. The challenge in 2021? Continuing to play this balancing act of cutting expenses, holding your money accountable, building up reserves, and investing into the right people, products, and services.


One of the biggest challenges in business is people. Having the right people in the right position on your team at the right time. Another challenge is the balance between not over-staffing your team, but also having enough staff to help the company grow (and not overwork current staff). As I mentioned above, investing into people is one of the best investments you can make – as long as they are the right people and as long as your business can support it.

I believe another one of the challenges in 2021 is actually going to be the abundance of talent. The national unemployment rate is still the highest it’s been since 2014, at 6.7% as of November 2020. It will be tempting to invest into new staff (possibly at a lower salary than they may have demanded a year ago). But that “discount” on top talent is only a good move if your team needs another hire (see the section above on Money). Stay the course and hold your money accountable and only invest into a new team member if your team is maxed out and you know that an additional hire will get your team to their next level of growth and profitability.

The challenges in 2021 are going to be very similar to the challenges that all teams, companies and business leaders face on a daily and weekly basis – time, money, and people. 2021 will bring some unique challenges as we continue to navigate the pandemic, working from home, additional childcare, home school, and elder care needs, as well as the barrage of new technology to help us all do the aforementioned better and faster. One thing is for sure, these challenges will continue to fast-track innovation and industry trends, separate the great companies from the merely good, and help us all grow as individuals.

What challenges are your company or industry facing right now? What is your plan to navigate those challenges and come out ahead?

Like this post?

Share on Facebook
Share on Twitter
Share on Linkdin
Share on Pinterest

Leave a comment


Recent Posts


We won’t flood your inbox. Opt out anytime.