At the small conference table in his new director’s office, Kevin confessed, “I feel so confused, and I’m just a failure at this.”

Everything began to spill out: He didn’t feel supported. Other departments demanded things he just had to figure out on his own. So he was creating goals and tasks that could prove his value, but he’d find out later it wasn’t what others wanted. And worst of all, maybe he’s just not cut out for this career, and it’s time to leave.

My client Amanda, Kevin’s new director, sat on the other side of the small conference table from her new team member, empathetic and flabbergasted. This incredibly capable man not only felt unsuccessful and disconnected, but Amanda realized he was now a less productive employee for the organization.

Wisely, Amanda leaned into curiosity and asked, “What makes you feel successful?”

Feeling successful at work has everything to do with your personality. Just like Kevin, trying to get to success brought out the worst of his personality. The worst of personality is called the shadow side. 

When you’re in the shadow, you will slowly move down from thriving and flourishing into an unhealthier space of struggling and languishing.

What that looks like, much like in Kevin’s experience, is wasted time, trying everything to get that feeling of success, but still feeling trapped because you don’t know what the target is. Your personality is in overdrive, out of control, like Dwight driving the work bus. 

Clearly, this doesn’t help you as a leader or the team accomplish its mission. Relationally, it costs you because those lack-of-success feelings begin to erode trust.

So nobody wants that, right? But what’s the other side of the shadow? The light. The light is the best part of your natural personality in a space of thriving and flourishing. 

There’s a little balance here. Shadow and light are connected. So as a leader, your tightrope is to move toward the light without encouraging the shadow.

As a leader, your tightrope is to move toward the light without encouraging the shadow.

Here are three tips for how to walk that tightrope for each Enneagram type. What the shadow side looks like, how to move toward the light, and how to lead each type.

Helping Eights Feel Successful at Work

The shadow side: You are going to protect yourself by controlling. If you don’t feel successful, you will likely challenge authority or just take charge — possibly alienating people in the process.

Moving to the light: See your role as part of the team. Take the time to ask questions to see what is expected of you, rather than just assuming you have the answer and start acting.
Leading to the light: Eights must trust the leader. If they don’t feel successful, you may end up in a power struggle because Eights will make sure they won’t be betrayed by you. They will do what they need to not get thrown under the bus. Make sure you are transparent: good news, bad news, no news. Show them exactly how you want to use their gifts, as well as what is their responsibility and what is not. That clarity will give them confidence and increase their feelings of success.

Helping Nines Feel Successful at Work

The shadow side: Fighting for success is exhausting and feels like disharmony. When you feel unsuccessful, withdrawal and disengagement feel so, so cozy. Another way this feeling shows up is a lot of busy work. Activity to be doing something, but it’s just movement, not progress toward solving the problem of feeling unsuccessful (and may be contributing to the problem!).

Moving to the light: Lean into your desire for fewer decisions. Define a clear goal and create a simple for yourself to accomplish that goal. One that feels doable and requires few decisions or steps along the way. Ask for help and clarity rather than withdrawal.

Leading to the light: Nines want to know that their success isn’t at the cost of someone else. That success doesn’t mean disharmony or disconnection. Success also needs to be clearly defined with their input. Include their voice in the goal and the timeline for completion.

Helping Ones Feel Successful at Work

The shadow side: If you don’t know the rules or policy, you create rules so you feel in control. The trouble is your Inner Critic is loudly saying that isn’t good enough. At the same time, you’re resentful no one else is following your (unspoken) rules.

Moving to the light: Ask for clarity if you are unsure. Feel free to bring your details, but also allow the process to be more simple than you make it.

Leading to the light: Help a One see clear action steps and what exactly they are responsible for. If there are specific rules, policies, or compliance, make sure the One has that resource and respect them when they bring those to you. They want to do what’s right.

Helping Twos Feel Successful at Work

The shadow side: You will start to overfunction, overextend, and blow all your boundaries just so you can feel some appreciation and gratitude for your work. And if that doesn’t come, you’ll add martyr to the list and still be overextended trying to get people to notice your work. 

Moving to the light: You don’t need appreciation to have significance. Also, just because a thank you is absent, doesn’t mean your work isn’t valuable.

Leading to the light: Specifically show gratitude for the work of a Two. Be specific in your praise in the way that person likes to be appreciated (verbal words, a note, a gift, some time, etc.). Tie your appreciation not only to your personal connection, but also to the larger business goals and how it benefits the Two. Especially show appreciation when they set healthy boundaries and ask for help.

Helping Threes Feel Successful at Work

The shadow side: You will hustle for a goal because you believe you have to hustle for your worth. So you will set goals for yourself and others that may not be in line with your organization or team just so you can feel successful. When that doesn’t work, confusion and feelings of failure keep you spinning, doing other tasks and trying hard to prove your worth.

Moving to the light: Failure is part of the process, not something that inhibits it. Ask for help in clarifying the goal, and use missing the goal as a lesson to help you succeed the next time.

Leading to the light: Threes need to know what the goal is, including the markers of what meeting the goal looks like. Encourage them as they meet the goal, but also help them see how to adjust as the goal needs to change.

Helping Fours Feel Successful at Work

The shadow side: You will push and pull, push and pull, push and pull to be noticed for your contribution. You might even create a bit of drama if you feel as if your contributions are unseen. Or you may retreat and stop creating until they notice your contribution.

Moving to the light: You can’t help but be yourself and be unique, even if others do not see it. You work in alignment with your authenticity and values.

Leading to the light: Fours feel successful when activities are tied to authentic values and see their unique contribution to the workplace. Help them tie their work to values and purpose with a mix of how they uniquely (and specifically) make the work better.

Helping Fives Feel Successful at Work

The shadow side: Your desire for knowledge and competency will lead you to data to demonstrate your success or a search for more information to prove your success. And if your thoughts are ignored, you’ll be tempted to go find more data to prove it. This keeps you on a hamster wheel, feeling incompetent and unheard, depleting your energy.

Moving to the light: Ask specific questions about what information informs the definition of success. Many people need less information than you do to feel successful or confident enough to move on. 

Leading to the light: Fives want to know their perspective and data is important and relevant. So if their information is ignored, then they are going to find more information to prove it and likely spend more time than necessary researching. Listen to their analysis, even if you go in a different direction. Help them see what information is relevant enough to make a decision and start acting.

Helping Sixes Feel Successful at Work

The shadow side: You are gonna work to not get blamed. So if the target is unclear, you will spin all kinds of scenarios, overthinking and getting trapped in preparing for all the eventualities you’ve created in your mind. Which can create a lot of extra work for you and others.

Moving to the light: All the preparations won’t avoid blame. Lean into your questioning ability to ask clarifying questions on what is expected and what is the goal.

Leading to the light: Sixes want their questioning (and sometimes pessimism) to be received as troubleshooting and problem-solving. If they don’t know what is asked of them, they will overthink and overprepare, wasting time and resources. Listen to their questions and help them prioritize likely scenarios rather than dismiss their concerns out of hand. They also want to feel protected. So if a Six does hold responsibility, talk to them privately and co-create a solution.

Helping Sevens Feel Successful at Work

The shadow side: If you don’t know what the goal is or why the process needs to be prescriptive, you’ll likely keep coming up with new ideas, because you want to find one that’s gonna make you feel successful.

Moving to the light: Every project has a boring part. You can push through that part to get to success. Sometimes you need support and reminders to get through the hard part to keep you on task and not avoiding with new, shinier things.

Leading to the light: Sevens need some freedom to feel successful. Guide them by being very clear and specific about the outcomes, and grant lots of latitude for process and method to arrive at the outcome. If you notice jumping for project to project or task to task, ask if they need any support. But also be open to letting them ask lots of questions and brainstorm lots of ideas. This will help them feel more confident in the direction that’s chosen. They’ve seen options and feel like the best choice was made.

I’m sure you’ve been on both sides of that small conference table: feeling like a failure and wanting to help someone toward their best success. Using these tools will move you into the light and lead others there too. And just imagine that feeling… a team of successful people helping others succeed. Imagine the innovation, creativity, and solutions that powerhouse team can create!

Using these tools will move you into the light and lead others there too.

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