start⬆Mngr handbook pt. 2: How to set clear expectations and motivate the team

start⬆Mngr handbook pt. 2: How to set clear expectations and motivate the team

First, a personal story…

On an ordinary afternoon, an A-player, superstar, technical genius on the team (let’s call her Casey), sent me an impromptu same-day meeting invite. I’ve always been suspicious of meetings without pretext. My guess was that Casey needed my help with something urgent, or wanted to communicate something special. In either case, it’s my philosophy was to deal with such situations sooner rather than later, so I simply walked over to the Casey’s desk and asked if they wanted to sync up right away.  She agreed.

Right after we settled into a meeting room, Casey told me that they had taken up a job at another organization.

This wasn’t a total surprise, as Casey had asked for a raise a few weeks earlier, which I declined (we have a company policy to discuss compensation annually, ensuring consistency for all team members). I went ahead and congratulated Casey on their career move, and out of curiosity, asked if they would have stayed on if the desired salary increase was given. Casey answered: “Maybe, but it would only have delayed my departure. I’m kind of glad I didn’t get it.”

I realized that I had failed to set clear expectations with the individual

That response puzzled me. Casey wasn’t leaving just because of pay (my initial assumption), but rather because they were unhappy with their job. How could this be? I had a trusting relationship with Casey, held regular one-on-one meetings, and had an ongoing professional development conversation, where we’d discuss her interests and try to find project opportunities that aligned with those. Aside from the salary issue, everything else seemed fine.

Why was this outstanding team member unhappy?

I got part of the answer by further chatting with Casey and reading her exit interview: Among smaller frustrations, Casey had no clear sense of what was expected, what success meant, and in turn, always felt unaccomplished. Interesting… I thought.

The question then begs… How could someone so successful, that I always praised feel that way? At every meeting, I only had good things to say: “I’m really happy with your performance”, “You’re rocking it”, “It’s a pleasure to be working with you.”

For weeks, I was trying to figure out how Casey could have felt unsuccessful. I then got another piece of the puzzle while randomly chatting with a colleague, a friend of Casey’s at the office:

“Casey was unhappy because there was always unfinished work at the end of the day, which she would continue at home, often disrupting her family life. She didn’t know when it was OK to stop. At the same time, Casey never really knew how well she were performing. Every time that you’d say “good job,” it added to the confusion and nuance: Casey simply didn’t understand what she had done that was so good.”

At the time, I didn’t really know what to make of this insight. But skipping ahead a few weeks, after discussing this with my leadership coach, I realized that I had failed to set clear expectations with the individual, failed to design a personal growth plan, and failed to be specific in my praising. The team member was going above and beyond relative to my expectations, but I failed to ever communicate what these expectations were. I’m not even sure if I truly had any expectations beyond working hard and doing their best. This left Casey constantly guessing about whether she was successful. And as most top performer in such a situation, Casey simply did more and more, better and better, without a clear goal. Over time, this likely drained her.

Upon further reflection, I realized that over years of formal education and examination, society has trained many of us, especially STEM students, to expect leaders to set clear goals and define success for us. We gauge our performance and areas to improve from report cards. We’ve rarely had to define success and set expectations by ourselves. So when we land a job where performance isn’t as clearly communicated as in a report card,  we feel lost. High performers that strive to beat expectations and earn A+ marks may not know how to interpret nuanced feedback, or gauge their performance independently. This is especially true for people straight out of school, and for jobs at start-ups where the definitions of success isn’t always clearly defined, and changes often over time.

It was my job as a leader to set personal expectations and goals for team members, and to help them continue their development. Even a simple expectation around timeline for projects or tasks would have helped the person understand what success looks like. Leaving people to independently figure out their success criteria may be asking too much if the individual has never done it. It’s a skill that needs to be learned. In short, I failed as a leader to set clear goals.

So let’s explore how to help team members define success and avoid confusion.

In part two, we’re going to discuss the basics of leadership. We’ll introduce a management system to help us maintain consistency in our interactions with team members, and explore important resources to help us:

  • Communicate clear expectations to team members;
  • Help team members meet expectations;
  • Track team member progress; and
  • Share constructive feedback.

What are some great reads on leadership?

The following two books provide a solid introduction on how to properly set expectations. I managed people for two years before being exposed these concepts, and certainly regret not having had this knowledge on day one. It’d have save my team and myself a lot of frustrations. They each take 45min to read, so we really have no excuse to skip them.

  • The One Minute Manager: The one minute manager (OMM) is a great basic management system that I recommend adopting. Having  a system in place helps us be consistent in our interactions. I’ve found the following concepts particularly handy:
    • Agreeing on expectations and goals early
    • Praising and reinforcing desired behavior and actions with specificity
    • Reprimanding if individual failed to achieve a desired behavior they have successfully achieved previously with specificity
  • Putting the One Minute Manager to Work: This one helps us implement the concepts explored in the OMM. While not as mind-blowing, I’m of the belief that success comes down to execution. And this book helps execute. What I personally found useful include:
    • 5 steps for training a learner to become a good performer
    • PRICE system

Beyond this point, I will assume that all readers have acknowledged the concepts introduced in the above readings.

How do I implement a management system?

The table below shows an example of how we can use the OMM’s PRICE system to plan and set goals.

In the context of management, the most used categories of goals includeproject goals (e.g. design a new feature / build a house), team or organizational goals (e.g. hit sales target, keep retention at x%), and individual performance goals (e.g. ability to query in SQL, ability to manage time independently). All three types of goals can benefit from the PRICE system as a way to agree on the specifics and keep track of our progress.

PRICE System Step Pinpoint + Record Involve Coach + Evaluate
Details of … Project goal OR Team goal OR Individual goal What are your expectations? Why?
What is the measure of success / performance?
What is your plan on sharing these expectations with the team member? What will you be looking to praise? When/how will you dedicate time / find time to praise? What will you be looking to reprimand and avoid? When will you dedicate time to reprimand?
EXAMPLE TEAM GOAL: Sales team goal Hit $50,000 in new monthly revenue to maintain growth at 25% over past quarter.

This translates into: 20 new leads per week per agent; $15,000 new revenue per week per agent.

Expose goal at beginning of month; showcase progress via email report weekly

Specifically, report on “% to goal completion” weekly and monthly, segmented by agent name.

Identify team members that are on their way to hit or surpass their goals.

Specifically, praise individuals that hit 70% of weekly goals by Wednesday, and those that surpass their weekly goals.

Personally speak with team members that fail to meet goals on consecutive weeks.

Specifically, look for lazy team members, and those that are holding less calls than others.

How do I set clear goals?

To ensure that there is clarity on expectations, I recommend adopting a SMART approach when setting goals. Being specific as to what we want to achieve helps to evaluate whether we’re making progress or actually achieved it.

What is the different between result vs. progress oriented goals?

Result oriented goals are achievements that one can hang on the wall: e.g. A series A investment into a company, a championship trophy, 5 years experience working at ______, etc.

Progress oriented goals are activities that we do while trying to achieve the result oriented goals: e.g. Improving the sales process at a company, training every morning to prepare for championships, taking a course to learn how to do a job or task better, etc.

In the context of setting goals, it is important to set both result oriented goals, as well as progress oriented goals. Whereas result oriented goals provide vision, progress oriented goals show team members a path to achieving the vision and feel successful along the way.

Assuming that a company’s end goal is to go IPO or hit $100M in annual revenue, it will likely take years to achieve its goal. So the journey needs to be paved with progress oriented goals that help team members feel advancement, see a path to success, and focus on learning relevant skills.

There are also many more opportunities to celebrate progress than there are opportunities to celebrate results, so teams that focus on progress are much more motivated. And when end goals are missed (which happens at the best of organizations), teams that focus on progress and have a growth mindset tend to reflect and make the necessary changes to try again, while teams that only focus on end results have a tendency to simply feel unsuccessful and beat down.

Other readings on goal setting I’ve found helpful:

How do I share constructive feedback?


As part of our job in helping people advance their professional development, we’ll come across situations where we wished an individual could have done better on XYZ. It may not always be easy to give such feedback, nor be accurately heard. Yet it’s our duty to actively give feedback, positive or negative. I’m therefore going to share a framework that can help achieve this without getting personal.

We explored in part one a communication framework to help assess whether a manager’s assumptions about a team member’s feelings are accurate. The same framework can be used to share feedback with an individual. Allow me to illustrate:

  1. First expose observations: As a starting point, we need to communicate specific actions, facts and events observed that led us to feel how we feel. These are non-negotiable and non-arguable elements. (e.g. I see that you’ve started participating and sharing your thoughts during brainstorming sessions on…)
  2. Next expose how you interpret these facts, your feelings: We will share how we interpreted these observations, and provide an opinion on whether the events were good or bad based on the context. (e.g. I’m seeing that as a sign that you’re really becoming comfortable sharing your thoughts and ideas with the team. Do you feel that way as well? )
  3. Give feedback on how to improve and grow: Finally, based on the events and interpretations shared, this is where we provide specific feedback to help an individual improve, call out something that we don’t want to see again, or call out something that we want to see more of. (e.g. I’m really happy that you’re putting the effort to frame your thoughts and sharing them with the team. I’d love for you to keep doing this. Please continue preparing your thoughts and allowing yourself to speak up at team meetings. Your ideas are very much appreciated.)

Special note on praising and giving positive feedback

happy face

Praising needs to start happening early in a person’s learning, especially when they get it right for the first time. It rewards good behavior, keeps them motivated, and guides an individual toward the ultimate target. When praising, it’s good practice to be specific in what a team member did well.

  • Specific praise: “Thank you for helping that client explore all potential options.”
  • Unspecific praise: “Good job with that client”

Relating back to results vs. progress goals, let’s also acknowledge that we need to praise both: Team members need to feel good about making progress and achieving results. If we only praise progress, it may undermine the need for team members to achieve results. And only praising results may lead to an unrewarding and even frustrating path to the end result, especially if it’s a long project, or if the end goals are still unclear.

Recommended reading:

Special note on reprimanding and giving negative feedback

 sad face

Reprimanding should only start after an individual has succeeded on a given expectation, and knows what “good” behavior looks like. It’s intended to reinforce good behavior once they’ve been able to achieve it.

Reprimanding before an individual has had a chance to succeed demotivates them and sets unreasonable expectations. How can we expect someone to get it right before they know how to get it right? It’s like expecting a person that has never skated in their life to win gold medal at the olympics for speed skating. Unreasonable. There is a process that we need to follow to properly guide team members toward success. We’ll explore how to coach and train individuals in part three of this handbook.

After a person has experienced success, a reprimand re-enforces the view that the goal continues to be important, that they have achieved it before, and that they can do better.

Similar to praising, reprimanding should also be specific:

  • Specific reprimand: “I saw that you dismissed a client’s idea before they had a chance to entirely communicate it. I’m disappointed that you failed to actively listen. You’re capable of achieving this as I’ve seen it before, so what happened?”
  • Unspecific reprimand: “I’m disappointed with what happened with that client.”

Recommended reading:

How do I make sure I’m heard?

be heard

While trust serves as a solid foundation to leadership, communication is our main tool. A leader that can’t effectively communicate their vision, their thoughts, or their decisions brings no value to the team: They don’t help set a destination, nor facilitate a solution to get there. As leaders, we must therefore learn to communicate effectively. Here are some outstanding resources on communication strategies to help us be heard:

Since most presentations today rely on digital slides or powerpoint, here are some good articles on how to avoid boring an audience:

If there’s one thing to recognize when giving a presentation, it’s that the audience can read much faster than the speaker can talk. With that in mind, I recommend to avoid putting into slides content that we plan to voice. Instead, slides should be used to complement what we have to say and emphasize a point: e.g. pictures, diagrams, or quotes that one wants to emphasize. This ensures that the audience is focused on what we have to say.

How do I make sure I’m understood?

Recommended reading: A case of misunderstandings

Saying something is not difficult. Saying it in a way that communicates the message accurately and that everyone understands is difficult. Too often, what we say is interpreted differently by different team members.

To be an effective communicator, we need to simplify and clarify.

Simplify the message

One method to simplify a message is to write it down and to strikethrough every element that doesn’t add value to the core takeaway. Any content that doesn’t directly help communicate the main message distracts the audience.

It’s a good idea to test one’s speech with a colleague to see if they remember the main takeaway that we intend to communicate. A simple message should be easily remembered and repeated by others.

Clarify the message

Beyond a simple message, a clear message ensures that the audience interprets the speaker’s words the way they are meant. This is accomplished by:

    1. Asking a member of the audience to repeat what we said;
    2. Providing relevant examples or analogies to illustrate the concept;
    3. Showing case studies to put things in context;
    4. Answering questions to clarify any confusions.

As best-practice, it is recommended to always communicate why: At the beginning of any message, simply describe why we’re here, why are we talking about this, why this is important, etc. This ensures that everyone is on the same page as to our goal.

How do I make the time to lead?

time agenda

To put the OMM management system (or any management system) into practice, we need to make the time to observe behavior, review work, prepare feedback, etc. More importantly, we need to recognize that this is part of our job, our time commitment.

Yet finding and dedicating time to managerial duties can be a challenge for all managers, especially new managers that may still be used to prioritizing individual work.

One solution is to schedule and block time for these tasks on the calendar, and respect it (this latter part is hard). Another tip is to be specific in describing managerial tasks to accomplish, helping to set clear scope to a task.

  • Specific task: Observe when a team member achieves _____ and praise.
  • Unspecific task: Observe team member behavior.

It’s important to realize that managerial work take more time to accomplish, so there is often no immediate reward. Individuals transitioning into leadership roles from non-managerial roles may find it particularly difficult to not feel instantaneous gratification everyday. To help with this change, a new manager can breakdown milestones into smaller tasks to feel constant progress. And to feel rewarded, I encourage everyone to celebrate every small accomplishment (e.g. give yourself a cookie every time you finish writing a chapter of the team’s quarterly report).

Recommended exercise

Let’s take some time to ask each team member: “Do you know what the success criteria are in your role?”

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