I’ve always struggled with employee performance coaching. I wanted to set clear employee goals and give direct feedback, but somehow I could never put all the pieces together at once. Feedback without goals felt like complaining, and goals without feedback felt like wishful thinking. This created a big tension for me as a caring, empathic manager.

Through years of trial and error (mostly error) managing people as a CTO, I’ve finally uncovered a concise set of principles that seamlessly combine employee goals and feedback!

In a previous post, I outlined how to prepare for feedback communication. In this post, we’ll examine how to execute your feedback conversation and expand it into a meaningful discussion of employee goals.

ACE Your Employee Goals!

You’ll approach the conversation in three phases:

Ask. Always start with a question. ALWAYS👏 start👏 with👏 a👏 question!👏

Connect. Guide the conversation by linking observations (not judgments) to their words.

Expect. Be clear about outcomes.

Plan for an hour. Half an hour isn’t enough, and you’ll get antsy after an hour. Don’t rush it; if you run out of time, you can always schedule a follow-up.

And remember, employee goals are a collaboration. You’re setting the stage, creating structure, and providing guardrails around the process. This gives the employee autonomy and support, while helping them arrive at goals that support the larger organization.

Ask: Create a Safe Atmosphere For Growth

Starting your feedback conversation with a question builds trust and rapport and cultivates a growth space. You need them to know you’re interested in their thoughts and you’re on their side, so engage in this discussion! Show you’re listening. Ask clarifying questions, deepening questions. Seek the core of their ideas. Let the conversation flow for at least 5-10-15 minutes before starting to Connect; you want to give them time to get comfortable opening up.

While you’re discussing their views on your topic area, look for hooks that correspond to your Observations - you’ll use them to transition from Ask to Connect. You can always refer back to the hooks later, you don’t have to jump on them immediately. Record especially relevant snippets verbatim, so you can Connect directly to their own words later (as a clarification, not a trap).

You’re trying to map their mental space so you can frame your feedback using their own mental model. This deepens the relevance of your feedback and enables intrinsic, sustainable change.

Connect: Interpret Observations Together

Now that you’re playing on a field they’ve created, use your observations to gently guide their thinking. You want to be like a potter at the wheel rather than a blacksmith at the forge. Allow the employee to influence your judgments as they offer their own data points. After all, this is a collaboration.

To help this phase feel natural but still keep things on the rails, I use four tactics:

1. Enhance when they say something I like. Agree with them, repeat what they said in my own words. Add observations that support their point.
2. Challenge ideas holding them back. Literally say “Can I challenge that?” and mention a relevant observation that encourages them to rethink their position.
3. Question again when they haven’t yet led me into an area I want to talk about and the current thread has dead-ended or started circling.
4. Reframe if I want to bring my own perspective to the discussion. Combine a few hooks to triangulate a new idea for them. Since this explicitly puts me in the driver’s seat, I use it sparingly (mostly when the first three are taking too long).

Some observations naturally land more forcefully than others. Deliver challenging observations tactfully by keeping them objective and impersonal. These are the most sensitive and difficult moments - you must remain on the employee’s side as you help them process new information, while also standing firmly confident in your observations. The conversation may change the interpretation or importance of an observation, but the observation itself is yours: your thought, your perspective, based on your experience. Save your flexibility for supporting the employee’s goals; rewriting the past doesn’t help anyone.

Expect: Set Concrete Employee Goals

Alright, you’ve spent 30-45 minutes or more tilling the field; it’s time to plant the seeds. Pivot the conversation to the future.

Take a break if you’re coming up on the 1-hour mark. These are intense conversations, you’ll both need a break, and the employee needs a chance to absorb everything. Better to end on a high note and schedule a follow-up than burn them out with a marathon session.

Approach this phase with a continuation of the ask-and-guide mentality, and shoot for two or three SMART goals. Since the first two phases focused on topics that you chose, the employee will naturally be thinking about goals in those areas! They’re likely to suggest goals that both satisfy your expectations and feel achievable.

If not, you may need to escalate the directness and force of your guidance. Escalate carefully, and strive to remain objective and on their side. Ultimately you can force them to adopt a goal you set, but they won’t get far without their own passion. The best goals are ones you both strongly believe are achievable and impactful. Any goals that you bring to the table need a killer pitch to achieve buy-in from the employee. Luckily, you have a detailed picture of how they see this topic that you can use to craft that pitch if necessary.

Do NOT allow the employee to set goals that don’t align with the needs of the company! The employee wonders why they aren’t promoted even though they achieved their goals, you wonder why the employee isn’t effective, and everyone gets frustrated. They can set personal goals and do whatever they want on their own time, but performance at work needs to advance the interests of the company as well as the employee. Redirect with a yes-and: “Your idea is great; you also have a big opportunity at our company by doing XYZ and I want to see you get the biggest impact for your effort.” A little open honesty goes a long way.

Bonus: Keep The Ball Rolling With Easier Feedback!

One more absolutely critical point:

WRITE. IT. ALL. DOWN.

Referring back to this conversation, their mental map, and specific outcomes they’ll pursue, directly supports your daily coaching. You can relate specific scenarios to the bigger picture, discuss various options for a situation and how they might play out, and meaningfully celebrate wins in real-time. Connecting employee goals directly to real-world experiences amplifies your message over time.

Don’t push your advantage! Celebrate with someone when they get a win through your suggestions. Even point out to them the wins they might not see. I know, you’re excited to see your suggestions working, but hammering every win with a moral basically amounts to “I told you so” - or worse, assumes they can’t connect the dots themselves.

When the next performance review cycle rolls around, being able to tie your new observations to concrete, specific, previously-agreed upon goals sets you up for another productive conversation.

You’re Ready To Set Employee Goals!

Together, high-level goals and concrete feedback create the structured environment and sustained effort that propels employees toward their potential. It’s hard to do well, but if you nail this process and you’ll stand out in their pantheon of impactful mentors.

What struggles do YOU face setting employee goals? Tweet me @archslide and share your story!