Project Practitioners > Challenge Directly

Challenge Directly

By Chris Cook, PMP

READ TIME: 5 minutes


Radical Candor, written by Kim Scott, delves into two important aspects of communicating with your team. Care personally and challenge directly are discussed in depth throughout this book. Combining these two elements of communication creates buy-in amongst your team and make you a ‘kick-ass boss.’


Here is a description of the book:

“Radical Candor is the sweet spot between managers who are obnoxiously aggressive on the one side and ruinously empathetic on the other. It is about providing guidance, which involves a mix of praise as well as criticism, delivered to produce better results and help employees develop their skills and boundaries of success.

Great bosses have a strong relationship with their employees, and Kim Scott Malone has identified three simple principles for building better relationships with your employees: make it personal, get stuff done, and understand why it matters.

Radical Candor offers a guide to those bewildered or exhausted by management, written for bosses and those who manage bosses. Drawing on years of first-hand experience, and distilled clearly to give actionable lessons to the reader, Radical Candor shows how to be successful while retaining your integrity and humanity.

Radical Candor is the perfect handbook for those who are looking to find meaning in their job and create an environment where people both love their work, their colleagues and are motivated to strive to ever greater success.”


Below are a few ways for you to start to challenge directly:


Delivering Hard Feedback

Delivering hard feedback involves telling people when their work is not good enough — and when it is. Challenging directly is not always negative. People need to know when they are doing well and poorly equally.

Be a presentation gone awry, or a report delivered expertly, both require direct, honest feedback from the boss. In the negative, make this a private conversation. Challenging somebody in public may turn a small criticism into a full-blown argument. The intention was well, but the environment was poor.

When challenging directly positively, make this in front of the team. Show the team how easy it is for you to deliver praise. The success is not about you. It is about the team member who put in the work and delivered the goods.

Difficult feedback needs to be well-intentioned. You are not calling someone out for the sake of a scapegoat. You are providing an example to the individual, and eventually the team, on how to perform better. The goal/project is the reason for your critique, not your +personal vendetta.


Making Tough Calls

When the team member is not going to get that new role he or she wankMed, or when you’re going to hire a new boss instead of promoting him or her. This news needs to be delivered by you directly to the person(s) impacted. An email is not enough.

Being a kick-ass boss involves doing the dirty work. No one enjoys firing people or breaking the bad news. However, it is a requirement of top-notch leadership to do so in a way that positively impacts someone even during the negative.

Part of the healing process from delivering bad news is the fact you told him or her face-to-face. There was not an assistant who delivered a memo. There was not an email sent late night so no one saw it until the morning. It was a conversation between the decision-maker and the person impacted.

If you care personally about this individual, the direct challenge will be welcomed. Present the facts. Remain objective. Give ideas on how to improve. If it is decided that this person needs to leave to get ahead, help him or her find the right fit.


Holding A High Bar

The results do not justify further investment in what they’re working on. Keep the justification to the facts. You set a standard at the beginning, and the team member is no longer living up to the standard. Both parties agreed early on this would be the measuring stick.

You have to let him or her know it is not working. Again, this conversation should be in private with the individual, not an email exchange across the entire team. Part of the conversation may be about you not holding up your end of the agreement too.

Challenge directly is not about the boss talking at individuals or the team. It is about radical candor on both sides. The team should also be holding you to a high standard, and if you are failing at upholding the standard, you should be called out directly.

This conversation shows the team you are not above criticism or the rules. You set the rules. Therefore, you cannot break them. This scenario is not always the case.



Radical candor, care personally and challenge directly, improves your leadership tenfold. You are no longer afraid to take a stand or deliver news or set standards. The best way to start this conversation is by asking your team for feedback. By showing you can take it and do something about it, your team reciprocates.

You care personally so you have their best interests at hand. It is not about liking or not liking. It is about the common goal you share with the team. You are setting a high standard, not to make yourself feel better, but to accomplish the goal of the project.

Once you establish the care personally aspect, you can challenge directly with a common understanding. Again, this is not about the person. It is about the project. The organization is better because a team member is not getting a promotion. It may hurt because you care personally about this person’s future, but putting him or her in too great of a role may have greater negative impact than the immediate promotion.

Care personally. Challenge directly. Be a kick-ass boss.

Not all comments are posted. Posted comments are subject to editing for clarity and length.

The comments to this entry are closed.

©Copyright 2000-2017 Emprend, Inc. All Rights Reserved.
About us   Site Map   View current sponsorship opportunities (PDF)
Contact us for more information or e-mail
Terms of Service and Privacy Policy

Stay Connected
Get our latest content delivered to your inbox, every other week. New case studies, articles, templates, online courses, and more. Check out our Newsletter Archive for past issues. Sign Up Now

Follow Us!
Linked In Facebook Twitter RSS Feeds

Got a Question?
Drop us an email or call us toll free:
7am-5pm Pacific
Monday - Friday
We'd love to talk to you.

Learn more about ProjectConnections and who writes our content. Want to learn more? Compare our membership levels.