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15 Bold Leadership Moves That Paid Off

August 14, 2017

7:15 am

Taking a chance is part of business. Staying static in how your company operates means, at best, your firm starts to slip behind others in your industry or, at worst, boredom and lack of creativity ends up costing you talented staff members.

But not every risk is worth taking. Sometimes what appears to be the path forward leads only to headaches, and your team is depending on you to make the right call. So how can you figure out how others have taken the leap?

To find out, we asked 15 entrepreneurs to share moments where they took a move that had a huge payoff. Here’s what happened:

Extending an Olive Branch to Major Competitors
Being that most adtech companies have developed proprietary technology, competition is fierce and sportsmanship is rare. As CEO, it is my job to constantly evolve the firm. Rather than engaging in undermining tactics, I extended an olive branch to competitors. While an uncommon move, it’s played out successfully for both parties, allowing us to create synergies and compliment each other’s strengths. – Jason KulpaUnderground Elephant

Embracing Confrontation
When I decided to stop resenting and start confronting, it transformed my workplace. Confrontation doesn’t have to be bad or even that uncomfortable, and it’s made it so much easier to communicate with my team. Now when something goes wrong, we discuss it immediately and it doesn’t happen again. My employees know I care enough to help them course correct, and I don’t stew about issues anymore. – Maren HoganRed Branch Media

Offering Transparency
The decision to embrace revenue transparency at Hubstaff was long discussed and extensively analyzed. We understood it was a big risk, but it has paid off in the long run. Being completely transparent has resulted in increased trust with customers and potential customers. It also keeps our team accountable: having access to metrics helps our team learn what works and what doesn’t. – Dave

Taking One Step Back to Take Three Steps Forward

In 2014, we pivoted the company from a web business to mobile business and laid off 30 percent of our workforce. Today, we’ve grown 10 times. We took one huge step backward in order to re-position ourselves for future growth. – Eddie LouShiftgig


Being Willing to Fire Customers

The customer is not always right. A bold move was when we emailed one of our largest customers and told them “We were not a good fit for them since our employee cultures did not match.” The background was that their staff was uncooperative and even condescending towards my team. The client replied right away, apologized and got their act together. It’s been a fantastic relationship ever since. – Nitin ChhodaTotal Activation

Going After Larger Clients

Because we were only growing, most thought we should wait to approach large potential clients, but I believed that we had the skill and capability to help them. By making this leadership decision, we were able to land a large client and more followed once they saw other big companies on board. It changed our results for the better. – Cynthia JohnsonIpseity Media

Betting on a Potential Trend

Earlier this year, my cofounder and I identified few trends that we believe would play out in marketing measurement industry in 2018. We then aligned our R&D efforts to build the product for the future, not today. It wasn’t easy, as we have limited resources, and we had to let few clients go as they did not align with our vision. We have already started seeing the demand for this new product growing. – Shilpi SharmaKvantum Inc.

Merging When the Time Was Right

One of the best decisions we’ve ever made was to merge my previous company with a company that offered complimentary services to what we offered. While we could have done the work of the other team, we knew that the other team had quality people that would improve our business if we were together. This was a year ago and today, we’ve grown our statewide presence in our offerings. – Kenny NguyenBig Fish Presentations

Exiting a Business

I made the decisive move to exit one business completely and sell it off. I could see that the industry was maturing, so I took a leap and left to try a completely new industry, and it’s been a huge payoff for me and the team that followed with me. I ended up quickly growing the new business and am now in a more sustainable industry. – Peter DaisymeDue

Delegating Responsibilities

Delegating more of our responsibilities down to staff members was a good move. We didn’t feel confident doing that in the beginning, but since we have a few seasoned vets on board, we’ve had them take over some of our non-essential responsibilities. That has allowed myself and our co-founder to have more time to grow our business. – Andrew SchrageMoney Crashers Personal Finance

Being the Stickler

We started with an all mobile team, so it was a pretty free and fun environment when it first started. At every stage where we’ve done better, I’ve had to crack down on the “organic” way of doing things, and convince people to follow more annoying, but more sustainable, standards. I was worried about how these decisions would affect my team, but they were with me for every change I needed to make. – Adam SteeleThe Magistrate

Stepping Away From Making Sales

In my business, I was making the majority of sales. Even with 15 people on our sales team, I was solely responsible for closing the majority. I realized there was no way the business could scale that way. I “ripped off the Band-Aid” and started passing off my entire deal flow. The result? My team closed as well as I had been, and I freed up most of my time to work on the business. – Erik HubermanHawke Media

Outsourcing the Call Center

Most people would never guess we outsource our call center. Why did we do it? As a garage door company, it is hard to find A-plus players who know how to book calls and dispatch properly. We gave a national call center a little test try, because they knew our CRM as well. They passed with flying colors, so we outsourced. Now all calls are a variable cost: no PTO, no employee tax, no parking issues. – Tommy MelloA1 Garage Door Repair

Opening Up About a Difficult Situation

Confidence is a pillar of leadership, but people think this means never displaying any sign of weakness. I think one of the easiest ways to garner respect and have your employees realize that you’re human is to open up about a difficult situation. If you’re not hitting the revenue numbers you need to hit, let them know! People tend to figure things out, so be open and honest — they will join you! – Bryce WelkerCrush The CPA Exam

Slowing Down to Focus

When we launched our company, we started pushing on almost every idea we had, with a big vision of building of lots of different companies quickly. We were spread way too thin and bit off way more than we could chew. By the end of our first year, we realized we needed slow down, scale our ambitions back and focus, which allowed us to successfully develop Beverly Hills Chairs and Custom Tobacco. – Adam Mendler, The Veloz Group


Read more leadership advice on building a business at TechCo

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