Build Your Leadership Skills as an Entry-Level Employee: Interview with Cy Wakeman #SHRM18



As an entry-level employee who wants to grow professionally, you hear constantly that you must build your leadership skills. What does that even mean, and how do you know you’re building the right leadership skills? I interviewed Cy Wakeman, an international speaker on leadership and management, and President and Founder of Cy Wakeman, Inc. She has a fantastic and authentic philosophy of leadership, and I’ve shared major takeaways from our interview below, including what not to learn from your manager, how to request and handle feedback, and tips for women. 

(For HR professionals attending the 2018 SHRM Annual Conference & Exposition, Wakeman will present a mega session titled “How HR Leaders Can Cut the Cost of Drama, End Entitlement and Drive Big Results.”)

The number one bad habit you should not learn from your manager

Too many managers have the bad habit of sympathizing, says Wakeman. Don’t copy the sympathizing behavior. Sympathizing is when your manager affirms you’re struggling and agrees that you are the victim of your circumstance. Empathy is better, she advises. Empathy is when your manager says, “I see you’re struggling and now I’m going to move you into self reflection and move you up to greatness.”



Wakeman gives an example. Imagine your see a pedestrian walking while texting. They trip and fall. Sympathy is to get on the ground and say “Oh no! These streets are not built for texting pedestrians.” Sympathy, however, would be asking if they’re okay but then asking what might be a solution to allow them to text without taking their eyes off the sidewalk. When your manager sympathizes with you, says Wakeman, they are colluding with you and together you decide the circumstances are the problem. “The circumstances are not the reason you can’t succeed, they are the reality in which you must succeed.” A great leader, she says, calls out what skills you need to move beyond the challenges.

Wakeman’s advice is to look for mentors that will help you grow, not collude with you. A good mentor who helps you hold yourself accountable will build your leadership skills.

Mentors are fine but you can do better 

If your employer has a mentorship program, don’t assume that your mentor will pave the right career path for you. There is danger in having one, or even two or three mentors, warns Wakeman. “It’s wonderful to have a few key mentors but know that it’s a super mixed bag. Why not use a crowdsourcing form of mentoring? Stop looking for the whole package in one person, because 50% of how they got to their job is pure luck and privilege.”

She sees people put too much faith in our mentors. By relying on a mentor, you’ve narrowed down all the possible advice from the whole world down to just a few pin points of career advice. Instead, says Wakeman, you should be a good curator of blogs, podcasts, and conferences. Build your world view.



A crowdsourcing approach to mentoring helps with networking too. You don’t necessarily need a profound relationship with one mentor to tap into his or her network. Wakeman says, “There are a lot of ways to get an introduction.” In fact, she warns that mentors who know you very well might share too much. That is, they might share your weak spots. Wakeman likes to mentor people herself, but just for a short amount of time and with clear cut goals.

Advice for young women to show their leadership capabilities

Research tells us that women face a double-edged sword as they climb toward leadership positions. They get turned down for leadership positions for not displaying “traditional” (masculine) leadership qualities, and they are punished in their careers when they do display those very qualities. Wakeman advises young women to get away from that story. “If you’re trying to change your behavior to manage what other people might perceive, you’re a long way from authenticity.”

Also read: Tips for entry-level job seekers to help fight sexual harassment 

In her own career, Wakeman says she “stopped trying image manage a long time ago.” When you worry too much about perception, she says, it quickly becomes the only narrative in your head. Instead, pay attention to how you can help other women and men.

She gave an example of how she has done this herself. She noticed that in meetings, women’s ideas were passed over, and men who suggested the same idea were commended. Instead of getting upset, she and other women decided to help each other out. They began to reiterate and back each other up in the meetings, saying “Can we stop and go back to that? I love that idea and want to build on it.”



People often ask for the chance to show that they add value. It may not be fair that others are privileged enough that they are given this chance without having to prove themselves. Wakeman says to think of it this way instead: “Once you add value, then you have the confidence to ask for what you need.”

Build your leadership skills by seeking feedback–but the right way  

Don’t go to just your manager for feedback, because you’ll only get information filtered through one lens. Instead, collect many data points of feedback. Go out and ask the same question of 10 people, advises Wakeman. “If you see something as just one data point, it doesn’t take a lot of courage to ask for it. If you see it as a mandate on your career, it takes all this courage to ask.” Ask for it in the moment too. For example, right after a meeting you can ask, “what could I have done better to facilitate that meeting?”

Wakeman’s advice is to get feedback by doing three things: 1) Make little tiny asks, 2) Ask for it in the moment, and 3) Do it conversationally–don’t request an hour-long meeting that will put a pressure on someone to come up with profound feedback.



Feedback is short but the opportunity for self-reflection is long. We often get feedback and instantly think how it’s wrong or misled. Wakeman advises people do an exercise when they receive feedback: Focus on how it could actually be true. To be mentally flexible like this, you must do self reflection. Self reflection is a practiced and learned behavior. Why not start practicing in college? Wakeman suggests you surround yourself with people who don’t feed into a corrupted view of reality that just protects your ego.

Develop yourself outside of your job and organization

Moving up in your organization isn’t the only way to build your leadership skills. Wakeman’s advice is to get a side hustle. Find out what you’re fascinated with. Volunteer or serve on a board. “It’s not even about building your resume anymore. It’s about how you’ve evolved and whether you’re a global citizen. Do you bring the whole package to work? Do you know how to learn? Are you aware of what’s going on in the world? Are you aware of your unconscious biases?”

Self reflection is important here too. You must reflect and understand what you have learned from your experiences so that you can articulate and market those skills and attributes. Employers certainly want to hear about how you have achieved results, but Wakeman insists that you also focus on other competencies. For example, if you were the captain of a successful college sports team, don’t just focus on the end results. Describe how you were able to inspire others to move beyond a challenge. That sets you apart.

Also read Networking: A Definitive Guide for Students and Grads to Succeed in the Job Search

None of us have experience in what’s next, says Wakeman. All of our jobs are going to change anyway, so get away from obsessing over what you’ve done.

When is it time to push your own ideas?

Wakeman stresses the difference between confidence and ego. She says ego is, “I know the way.” Confidence is “I’m confident in some of the things I can bring to the table.” If your priority is to protect your ego when things don’t go your way, you end up narrating to yourself that you’re undervalued. Instead of focusing on failing, you need to manage how you can make something work. At work, don’t negate something you don’t agree with. Build on those ideas by suggesting, “What if we did this…”

Show up and offer what you can, says Wakeman. That is authentic. Don’t go in with guns blazing. If your awesome idea didn’t get picked up, write about it somewhere else. Neuroscience tells us that people need to hear ideas several times anyway. Trust the process, she says, and work with those who are willing. “Stop trying to convert the biggest nay-sayer. You don’t need consensus. You need to connect with people who resonate on a similar frequency. Those small groups are what get business done anyway.”

 Cy Wakeman

Connect with Cy Wakeman on LinkedIn. Cy is a globally recognized thought leader and dynamic keynote speaker. She delivers keynotes and training on many topics, including:
– How to ditch the drama and turn excuses into results

– The essence of building resilience and bulletproofing your employees

– How to hardwire accountability into your workforce

– Why employee engagement is the true driver of employee performance

– The new leadership foundation for boosting employee value, driving strategic results and fulfilling organizational missions


Originally published on College Recruiter blog.



The SHRM Blog does not accept solicitation for guest posts.

Add new comment

Please enter the text you see in the image below: