Uncomfortable talks for career success

How to Have Uncomfortable Talks to Realize Career Success

Success in life is rarely about taking the easy road. Often, you have to step outside of your comfort zone, both personally and professionally, to achieve your dreams. True breakthroughs come by taking risks: asking your boss for a raise or promotion, or confronting dissatisfaction with a significant other.

But taking bold steps can be stressful. If you haven’t been there and done that, you’ve no clue how things will turn out on the other side. As Tim Ferriss wrote in The 4-Hour Workweek, “A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.”

Bottom line: You never know what’s possible if you don’t take a risk.

Difficult Conversations: The Secret to Success

According to SoFi Career Strategist Rachel Kim, when it comes to career success, three of the most difficult conversations are:

  • negotiating a salary or raise
  • asking for a promotion
  • discussing problems with co-workers


Related: Four Ways to Build Your Career Through Conversations

Research shows that these tough talks generally create positive results. Right Management surveyed managers and employees from 15 different countries for a 2016 study called Talk The Talk: How Ongoing Career Conversations Drive Business Success, and found that “two-thirds of individual performance drivers are tied to Career Conversations, making it the most important people process in an organizational culture that embraces career development.”

That same study found that if career conversations were more regular:

  • 82% would be more engaged with their work
  • 78% would be more likely to share ideas
  • 76% would more likely seek career opportunities with their current employers
  • 75% would more likely stay with their current employers


But despite such great numbers, only 16% of those surveyed said they have ongoing conversations about career development and workplace performance with managers. So if your boss isn’t going to initiate those discussions, it’s all up to you.

Four-step Prep

The steps below can help you prepare for career and life talks you anticipate will be difficult. “Be honest,” says Rachel. “Put it out there—acknowledge that it’s probably an uncomfortable situation for both of you. That should go a long way to get rid of the elephant in the room.”

  • Schedule the conversation well in advance. This gives both parties time to organize their thoughts.


  • Plan what you’ll say. List your talking points before the discussion. It’s sometimes easy to forget to hit on important issues, especially if the conversation doesn’t go as planned.


  • Consider the other person’s perspective. Don’t go into a conversation thinking you know exactly what the other person will say. Let him or her speak, and then listen, listen, listen. Don’t miss out on what’s being said because you’re stuck in your own expectation and/or your thoughts are racing.


  • Be positive, not defensive: If you’re coming from a place of fear, anger, or worry, it’s easy to get defensive and cause a communication breakdown. If you start to feel tense, breathe deeply, and stay calm and centered in the moment to avoid saying something you’ll later regret.


Overcoming Resistance

Even though you’ve planned the conversation, you might still resist going through with it. Rachel offers these suggestions if you feel yourself starting to balk:

  • Learn to change your mindset. When you’re stuck and want to shirk away from your game plan, there are skills that you can develop to help you push through. “Go from a fixed mindset—believing that intelligence and talent are set from an early age and unchangeable —to a growth mindset, in which you believe you can become smarter and get better at something if you focus on it,” says Rachel. For example, if you fear negative feedback simply because you’ve always feared it, reframe that thought: Affirm that you’ll be getting constructive criticism that you can learn from and incorporate into your work.

Recommended: 5 Expert Tips to Landing a Big Promotion in 2017

  • Rehearse. Role-play best- and worst-case conversation scenarios with a friend or trusted colleague. Anticipate all that could happen, and the focus on what you learned. Chances are much of what you’ve practiced will come into play.


On the path to professional and personal success, you’ll need to take some conversation risks. By learning how to navigate the hard talks and your own discomfort, you can avoid the obstacles that can get in the way of reaching your career and life goals.

Talk to the SoFi Career Coaching team to learn more about how you can advance your career.

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