3 Tough Conversations Every Leader Must Face


by Sumi Krishnan


Strong leadership takes guts. Don’t let fear of tough conversations bring your startup down.


There are few things more uncomfortable than having the “you’re fired” conversation — except maybe having that conversation when you’re one of the most prominent corporate leaders in America.




Earlier this year, Marissa Mayer attracted a lot of media attention when she fired COO Henrique de Castro — her first major hire as Yahoo’s CEO. Some pundits were outraged by the millions in severance he walked away with, while others began speculating about how much longer Mayer would be at the helm.


For female leaders, it’s imperative that we don’t let the opinions or perceptions of others affect our decisions. Having the confidence for hard conversations is often what builds our platforms for success.


Here are some strategies to help address a few difficult discussions:


Difficult Discussion No. 1: Addressing Opposition From Your Team

As your company grows and adapts to new challenges, you’ll inevitably need to pivot your business strategy. But with change can come opposition.


If your team disagrees with your choices, it means you haven’t effectively communicated your vision. Fortunately, you can set the record straight and regain their confidence with one simple conversation. Instead of arguing or approaching each conversation with a “my way or the highway,” attitude, take the extra time to get your team on board. Paint them the big picture. And remind everyone where and how they fit into that picture. If it’s not clearly painted it’s your fault, not your employees’.


If, however, you’re just leading a team of negative naysayers, you must feel comfortable responding, “This is my vision and we’re sticking to it.” In this case you’ll also need to do some personnel evaluation — it’s important to have the right people on your team.


Difficult Discussion No. 2: Warning Slacking Virtual or Part-Time Employees

Despite the many benefits of working with virtual employees, falling into the trap of “out of sight, out of mind” can make it difficult to manage them effectively.


When employees aren’t accomplishing their tasks, it’s important that you don’t wait for them to self-correct. It’s easy to let too much time go by and suddenly find yourself buried beneath a mountain of issues. Instead, approach each challenge immediately. It will save you months of headaches.


Make sure each employee, virtual or not, has a checklist of her roles and responsibilities. As simple as it sounds, it’s surprising how many business owners and leaders don’t provide this for their team members. To keep everyone on track, schedule regular phone calls, hold Skype meetings and collaborate on Google Docs.


Most importantly, make it clear how much you care about their success as well as the company’s success.


Difficult Discussion No. 3: Telling an Employee and Friend That She’s Slacking

It’s hard to work with family, but it’s just as hard to work with friends. When your employees become your good friends, oftentimes they’ll start to take your requirements or expectations for granted.


Nip this in the bud as soon as it starts to surface. Make sure you set the record straight and tell them, “I know we’re friends, but I still expect you to follow through with your responsibilities to the company, and I just can’t give you any special treatment here.”


Always start these conversations with a friendly but firm declaration. For example:


Jane, even though I consider you a friend, I first have to honor our business relationship. Just because we have a friendly relationship, please don’t misinterpret that to mean that my expectations are going to be any more lenient. In fact, my expectations could be even greater because I have so much respect for you and trust you more.


If she’s a true friend and a good employee, she’ll rise to the challenge.


Unfortunately, there’s no cheat sheet for leaders that outlines the proper way to handle every situation. However, women don’t have to emulate what they’ve seen on TV or act more “like a man” to be taken seriously when these situations occur.


In this new economy — with the rise of social media and utter transparency — people want to be led by a real person, not a robot behind a smiling face. That means you have the freedom to define your own leadership style, follow your instincts, find your voice and stick to your guns. You know what’s right. You just need to have faith in yourself.



Sumi Krishnan is the President and Founder of K4 Solutions, Inc. a $20 million dollar consulting firm located in Greater Washington DC. Her firm works with clients including the Dept. of Defense, Dept. of State and Dept. of Homeland Security on functions including cyber security, records governance and call center management. She has recently launched a new business coaching program for women entrepreneurs and leaders — helping women leaders build successful businesses and make the impact they truly desire to make in the world. Sumi is an award-winning business woman and has been named to the Washingtonian’s “Woman to Watch” list and on the Inc. “30 under 30” list, among others. 


Originally published by StartupCollective.


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