Get Serious About Online Meetings — 5 Questions To Make Them Shorter And More Productive

Alessandro Montalto PhD
8 min readJan 6, 2021


You can use these five questions for every dialogue in your life, even with yourself.

I’ve always hated more-than-10-minute long remote meetings. They are draining and exhausting. In my experience, lengthy meetings lack one meaningful point: concreteness about what to do next and who takes responsibility for those steps. At the end of a two hour meeting, the conclusions are usually too vague and blurry to be of any practical use. Once you leave the online meeting, you are left with more questions and doubts than before the meeting.

Sounds familiar? Then this post is for you.

I already talked about how to have less online meetings and be much more productive from a more theoretical point of view. Here, I want to address this important topic from a much more practical point of view. I really want to give you the tools to enter any conversation, even with yourself, with a crystal clear overview of what to expect from it.

A common mistake

Before diving into how you can be more productive and shorten any meeting, it’s interesting to analyse what the source of having such extended meetings is.

The source that generates miscommunication, misunderstandings, disconnection, complicated and convoluted explanations in a meeting is a plain and simple lack of clarity. If you don’t have a clear idea of what you want to share, being it a problem that you want to solve or a successful story or a simple update, nobody will.

For the sake of explanation, let’s say that you want to solve a problem (the same approach can be easily extended to all the other scenarios) and that you want to get serious about any online meeting and make the most out of them. Then, you have to prepare before each conversation. There are no shortcuts, no sideways to sneak around the preparation. Your colleagues are devoting their time and resources to you. Being prepared shows respect and a team player mentality that will dramatically improve the connection with the team.

How do you get prepared?

By replying 5 simple questions. I designed them to give you the best possible outcome from any dialogue you can have in life. Thus, they can be broadly used, even when you talk to yourself and try to figure out what is preventing you from adopting certain behaviors.

Let’s analyse each question, see why it’s so important and understand what the implications for you and your team are.

1. What’s the problem (/success/update)?

That’s the most important question for you to answer. It’s the first question for a reason: you need to be have a clear idea of what the problem is. The best way to know when you nailed down the true problem is when you can explain it in no more than four sentences.

It sounds challenging, but it’s not really that difficult. Skip all the details, all the clutter and get to the core problem. You will notice that a big part of discovering what the real problem is has to do with your level of vulnerability. So, I strongly encourage you to explain the problem to yourself out loud and be as vulnerable as possible with yourself. You can also write it down if you prefer. Then, adjust the level of vulnerability that you want to bring in the team. And remember that vulnerability is the main building block of a great teamwork, so embrace it confidently!

By replying this first question, you will start any meeting by hitting the bull eye. Your colleagues will feel much more engaged from your very first sentence. You will be able to explain in a few words what’s at stake and what the obstacle is, grabbing the attention of everybody and redirecting it on the real problem, not on you.

The teammates will be grateful to you for the opportunity to use their brain to really contribute to solving a problem, rather than painfully trying to figure out what the problem is, aka doing your job. You will show a great degree of respect for their intelligence and trust in their support.

2. How did you try to solve it? (Why do you want to share it?)

This question is meant to give an exhaustive overview, please summarize it in as less sentences as you can. If your colleagues are willing to help, the best way to create ideal conditions is by providing them with useful information about what your strategy has been so far.

Share with them every solution you tried. The ones that seemed promising to you and the ones that really didn’t work. Why? Because in this way the team can already see whether your reasoning and approach can be improved. Maybe, you adopted a great strategy, but the way you carried it out was the real obstacle.

When you commit to answering this question, you will be naturally encouraged to point out the amount of work you constructively poured in finding a solution by yourself. It shows proactivity, self motivation, enthusiasm and great teamwork. It can also be quite confronting if you tend to think that you have to do more and be more. So, be always kind to yourself, just relax and enjoy this learning process.

Imagine how differently a meeting can go. So far, if you went into a meeting unprepared, you probably noticed either silence or a very poor helping attitude or, way worse than this, frustration whenever a colleague explained a possible solution just to hear a dry “I did it already and it didn’t work”. Help the team to help you. Make their job easy by giving them as much useful material to work with as you can.

3. What’s not working? (What’s the added value of this success/update?)

I want now to encourage you to be a bit more explicit about the problems that you needed to or couldn’t overcome while exploring the solutions you mentioned earlier.

Share with your team the most painful problem about each successful and failed strategy. Let them relate with you so that their feedback can be much more personal and experience driven. You will be surprised to see the empathy that your colleagues will show. In a remote work scenario, empathy stems from vulnerability, the vulnerability you are bringing in by replying this questions.

And vulnerability is the glue of every team. You know very well how needed empathy is, so make a forward-thinking move by being the first to tap into vulnerability. The rest of the team will follow suit.

4. What have you learned so far?

In other words, what’s your take-away from all the work you have done? What piece of knowledge do you feel like sharing with the team so that they can build upon what you went through?

Answering this question is crucial for the preparation of the online meeting because it really sets the example. It shows the team that you are an excellent problem solver who not only comes up with solutions, but can also analyse them and learn from what worked and what didn’t critically. Furthermore, the way you share your process to find the optimal solution shows humility and willingness to build an invaluable common knowledge.

If you keep your answers short and to the point, the remote meetings will take a completely different turn. You will add an enormous value to the work of the whole team. Enter the meeting with strength and humility drawn by the awareness that your are actively making an effort to both increase the quality and reduce the length of the meetings.

5. What do you want from the team (/yourself/spouse/friends/family) specifically?

Are you looking for feedback, opinions, creative thinking, funding, permission to create a spin-off project…? You entered the meeting to share something valuable and you are now asking for a fair opportunity to learn from the team.

Don’t be afraid to ask for help. Replying this last question shows your teammates that you know exactly how to work in a team where each member can get support. In the first four questions you created value for the team. Now, you are asking for an exchange of value.

This final answer makes clear that you want to give feedback mutually and openly. You are building a healthy remote culture where each single person is listened to and helped.

In the end, you are using these 5 questions to become an engaging, passionate and value driven storyteller who can summarize her learning process in a few sentences and is ready to bring the team on board. Furthermore, you are sending a strong message to your colleagues: I value honesty, vulnerability, empathy, communication and teamwork and I want all of us to build a solid remote culture by making the first step.

At the end of the online meeting, the whole team will have a clear idea of the state-of-the-art of your situation and who exactly can help you and how. By embracing vulnerability, you are bringing clarity to the team and the possibility to develop an action plan that is suitable for everybody. This means that the responsibilities, tasks and expectations of each member of the team will be well defined.

If you are still not fully convinced about preparing meetings by following these five questions, I can bring you the feedback of the CEO of the IT company Zupit. He told me that they adopted this approach right after I showed it in my workshop. Consequently, the quality of their online communication, either via email/slack/telegram or in a Zoom meeting, has dramatically increased.

What if you don’t get the promised results?

That’s a great question! Well, there can be several causes for a lack of improvement.

It might be that you didn’t really nailed the problem down and, consequently, all your answers still sound foggy. It might also be that your team isn’t ready for this approach. Another reason might be that you are probably too harsh with yourself and you need to be more patient. This approach implies building a new kind of relationship with your team. This means that there is a change ahead for all the teammates. And change, as I explained here, brings a grieving process. Allow the shift in perception to take place by being kind and patient towards everybody, especially yourself.

I would strongly encourage you to explore the way you answer the questions with curiosity and kindness. And if after some meetings you really don’t see any improvement, don’t worry because you can always reach out to me and we can explore together what’s not working. I understand that the questions imply some digging into your thoughts and values. Answering them can bring up some painful emotions and it’s normal to seek guidance. I am here to help you overcome whatever obstacle you can find and create a fulfilling remote work experience.

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Alessandro Montalto PhD

I mentor people to develop the required soft skills to become successful remote workers —