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  • Writer's pictureAmory Borromeo

The Secret to Amazing 1:1 Discussions

When I first start working with a new boss, I set expectations early and walk through the best approach for our relationship. I like to align asynchronously on projects, progress, and needs in order to reserve our precious time together for development and more complex discussions. Over the years, I have adapted this model and approach based on the dynamic of the relationship between my boss and me.

Similarly, as a leader myself, I have adapted this model with my team in various forms to create alignment, drive autonomy, and develop a sense of empowerment for my direct reports. Since this is a topic that comes up often during my speaking engagements and coaching session, I thought I would share my tips and tricks with all of you.

First, in order to enable one-on-one conversations to provide the chance to discuss development opportunities, you first have to create another avenue for developing alignment as it relates to progress, project status, and the like. This could be through various channels.

One example is a Weekly Activity Report (WAR) where you provide some level of the following based on what's applicable to your role:

  • Project/Program Status Update - How has the status changed from last week, what pivots or changes have been made, anything the person needs to be made aware of, and any needs or blockers to success/completion.

    • Recap of the previous week - List out what commitments weren't completed as well as any additional items that snuck into your week that were unexpected.

    • Commitments for this week - List the area(s) will you focus on this week and any specific deliverables you plan to complete. I'd recommend looking at your calendar and assessing your available time for the coming week when making new commitments. This helps ensure you'll be successful in completing what you are committing to.

    • Stretch/Backburner items - What would you do if you had more time? What is next up to do? Listing these items out allows your boss to realize how and what you're prioritizing, in addition to giving him or her an opportunity to change your focus and prioritization.

    • Personal Updates - these don't have to be included, but as a manager, I appreciate knowing how my direct reports are feeling and what challenges they are facing in their personal lives. This also allows me to help encourage a better work-life balance for my entire team as we recognize and appreciate team members who take time for themselves. This also allows me an opportunity to share details of my world with my boss, without having to have an uncomfortable conversation. This was especially important navigating through the changing world in 2020 and the challenges my family faced with Covid and the like.

In some cases, I would send this report before the end of the week in other instances I would send it first thing Monday morning, or end of the day Sunday. The timing is less important as compared to the consistency. If you decide to send it out at the end of the day Monday, do that every week. This ensures you're capturing the whole week and sets a clear expectation with your manager as to when it will be received. You may want to work with him or her to come up with a cadence that works best for you both.

Another option is to have a running document that is shared between you and your boss with all of your projects, programs, or similar commitments in one place. I've used sheets, docs, and even decks to manage this. Oftentimes, I'll combine this with the above WAR email. The intent of this artifact is to provide a way of tracking progress over time, which can be especially beneficial for reflections. (I'll post a separate post on reflections soon)

Okay, so now that we have an asynchronous communication channel to drive alignment on prioritization and progress, so how should we structure our 1:1 agendas? I'm a strong proponent that 1:1 meetings should be used for relationship building, professional development, and complex discussions that can't be handled asynchronously. A typical agenda may look something like this:

  • Constructive Candor/Feedback

  • Blocks / Needs

  • Complex Program/project updates

  • Professional development initiatives


Starting every session with feedback is such a powerful tool for development and relationship building. This requires a strong relationship built on trust, where both parties know that the intent is always centered around moving towards excellence. When feedback is viewed through the lens of making us better, we can put our ego and insecurities aside and benefit more from the constructive feedback.

Candor and feedback should always flow both ways. While it is always best to provide constructive feedback as close to real-time as possible, it is helpful to have discussions on that feedback in more depth. If you don't yet have that level of candor baked into your relationship, try asking pointed questions such as, "What were 2 things I could have done better in the presentation/meeting/etc.?" You may also share some specific examples of things you struggled with to solicit feedback on how you could have approached the situation differently. For example, "I was in this meeting last week, and I noted that no one in the room or on the virtual meeting was engaging in the discussion. I tried, X,Y,Z but that didn't seem to work. Do you have any suggestions on how I might approach this in the future or how I might be able to uncover why the group wasn't participating?"

You should also feel comfortable sharing that same level of candid feedback with your boss. You may opt to present it in the form of an opportunity to ensure it is constructive. For example, you may say, "I think the team has a lot of respect for your opinion and when you start the conversation with your input, then ask the group for theirs, it tends to result in groupthink, where people are less likely to share converse opinions and instead go with your direction. You may want to advise the group that you have thoughts but would like to hear their opinions first. This may result in a more innovative solution that differs or builds on your idea." See how much more constructive that is compared to, "You talk too much in meetings and no one else feels comfortable speaking as a result." Feedback should include an action or behavior, the impact, an example, and the preferred outcome and/or behavior that could drive that to that outcome.

The most important piece to feedback is being receptive to it and grateful to the person sharing it. It takes a lot of courage to say something that may hurt someone else's feelings, but when done from a place of wanting all parties to be better, it can be incredibly valuable. The more often this type of behavior is demonstrated within an organization, the more likely it is to percolate through the company to become engrained in the culture.


Very few people feel comfortable admitting they need help, least of all to their boss. It is difficult and no matter your level of ego, it stings. If we can meander away from this type of thinking and instead recognize these as opportunities for growth, we can continue to develop professionally. When we are blocked on something, people receiving that message are quick to action the solution. It is mostly inherent in leaders to try to solve problems. (This is most certainly an inaccurate generalization, but for the sake of keeping this post simple, we won't go into the nuances here.) So it is very important that you set expectations at the beginning of the conversation to enable the other person to best support your needs. Consider the following two examples:

  1. I'm blocked on this project because I can't make a decision on X. Can you help?

  2. I'm unable to make a decision on this project because I do not have the historical context or an understanding about X. Can you share what you know regarding X or point me in the direction of who may know more? That way I can gather the information I need to make an informed decision.

The latter is obviously much more empowering for the individual and an equally easy solution for the person supporting. It allows for the asking individual to gain the information needed to make a decision, which will likely allow that person to more easily make decisions moving forward. If you are a manager and you run into the first example more often, think of empowering questions you can ask that will allow you both to uncover an alternative method of unblocking the individual in a way that enables him or her to come up with the solution on their own.


When faced with a complex update or a sensitive topic, it is best to block time in a face to face session to discuss, as opposed to risking anything being lost in translation via asynchronous communication. If you have to re-write the matter multiple times and still feel nervous to include it in your WAR or similar documentation, it likely warrants a discussion. If you think there will be more questions as a result of the update, anticipate that and note in the WAR that you'll plan to discuss further in person.

Whether it has to do with a program status update, project progress or prioritization pivots, or some sensitive topic, provide what context you can upfront to spark the conversation and simply plan to address it during your discussion. This will oftentimes bleed into professional development as these more complex issues may require some support handling them. Take this as an opportunity to learn and grow, when possible.

While reserving 1:1 discussion to focus on development and relationship building is a great approach, the business needs should still come first. If there is a need to spend much of your time together, talking through a new project or issues on an existing initiative, recognize the importance and handle it accordingly. It is important to not be too prescriptive here and ensure your approach has plenty of flexibility to handle the things that may arise each week.


Truth be told, all of the above-mentioned discussions will result in professional development. These all provide lots of opportunities to learn and grow; however, I do find it to be beneficial to fully align on what you are interested in as it relates to your career trajectory and professional development.

As an individual, I try to keep my boss aligned with my interests and vision in order to allow him or her to afford me with meaningful opportunities. If he knows that I am interested in becoming a senior leader, he can then assign me projects and tasks that allow me to develop that skill set. If I tell my manager I may consider a career change as I'm interested in design, she may allow me to work on cross-functional projects where I can have more interaction with the design team to get a better idea of if that would be a good fit for me. The point is, if they don't know what you want to do, how can they support your dreams?

Most of you know that I'm a huge reader and love learning new things and applying them to my day-to-day. This part of the discussion is a great time to share the latest research I've discovered to get the thoughts of my leader as it relates to our business, industry, company, or even gaps we have on our team. Together we can think through the various ways we can incorporate it into our team or how to leverage it.

This is also a great chance to ask for more opportunities and better understand any gaps in your performance with the expectations of your role. Having this kind of conversation regularly allows for individuals to grow into new roles within the organization more quickly, as compared to waiting for annual or semi-annual reviews.

At the end of the day, the best professional relationships stem from those who are not afraid to embrace uncomfortable conversations and get vulnerable. Developing a strong relationship built on trust and empathy can allow for all parties to feel more comfortable getting and sharing feedback for the sake of developing operational excellence.

I encourage all of you to find ways to level up your one-on-one discussions to enable you to gain the most from the precious time you have together. I would also note that a lot of the framework shared here can be used for mentorship discussions and discussions with your peers. Keep an eye out for more posts related to both of those.

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