Conducting Effective One-On-One Meetings With Your Executive Direct Reports

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Some executives assume that they don’t need to have regular one-on-one meetings with their executive direct reports.  The idea that such meetings aren’t really necessary “at our level” is short-sighted.  What is not necessary is using the same one-on-one framework that you’d use if your direct reports were front-line staff.  What is necessary is a framework more appropriate to the needs of an executive and his or her direct reports.

I highly recommend a weekly one-on-one with each of your executive direct reports (we’ll simply call them “managers” for this post), being flexible when needed.  In addition to gaining valuable information that you need in order to be effective in your job, these meetings are a valuable way to help your managers understand the nature of your job and what you need in order to be successful.  By doing this, you’ll not only get valuable information that you need, but you’ll be grooming your managers as part of your own succession planning.

Here’s the agenda I recommend, in this specific order (I’ll explain why shortly):

  1. Needs: How can I help you?  What do you need from me in order to do your job?
  2. Updates: Make me smarter.  What do you know that I need to know?
  3. Professional Development: How can we use opportunities in your current role to help you develop for your desired future role?


One of the three things that leaders owe their teams is to remove obstacles.  Since execution and delivery are your team’s top priority, this is always the first item on the agenda.  By so doing, you’ll know where you can add the most value NOW should your one-on-one meeting get cut short.  They key question to be answered in this part of the meeting is, “What do you need from me in order to do your job?”


While you owe your team THREE things, your team owes you ONE thing; to make sure you have the opportunity to never make a mistake.  Your managers can do this by providing you key updates, based on your needs.  First, help your managers understand what you need to know, why you need to know it and what level of detail is required.  Finally – and this is key – help your managers understand how you plan to use their updates.

Help your managers understand what “success” means at your level and how they can help make you successful.  They do this by updating you on what’s happening in your area based on your needs as an executive, and to make sure you have the opportunity to never make a mistake.   Don’t let them bury you in minutia; keep it focused and productive.  This way, you not only get what you need to do your job but you make your managers smarter by helping them understand how they can help you.


Part of your role as a leader is to develop your staff to maximize their contribution to the business as well as to foster their personal development.  Start by using the ‘Greed/Fear’ Framework to understand what each manager wants professionally and personally.  Make sure you understand their short-term (current role) and long-term (overall career) goals. 

Typically, business technology teams perform in one of three work streams:

  1. Operations and Production Support
  2. Policy and Procedures
  3. Projects and Initiatives 

Frame each development opportunity within the relevant work stream so that you can provide feedback and development opportunities for your managers within the context of businesses needs.


Investing in our teams is an important part leadership.  This is even more important when it comes to our executive level direct reports.  A well-developed management team functions as your personal brain trust, helping you be a more effective leader.  Such a management team also will earn the trust and confidence of your business partners and also from your managers’ respective organizations.  You’ll also be grooming your managers so that you can ensure a smooth succession when your next opportunity arises within or without your current company.  Take the time to meet with your managers on a regular basis and make sure you use a framework that meets your needs as a leader AND the needs of your managers as aspiring executives.

© 2011, Mark E. Calabrese

Greed and Fear: Part II – Applying the Framework

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In Part I of this post, we said that the ‘Greed/Fear Framework’ is focused on understanding others and is driven by a genuine desire to invest in others by actively listening and by empathizing.  This is easier on the ‘Professional’ level than on the ‘Personal level’.  Let’s look at an example:


Your business partner is responsible for Call Center operations in your firm.  The Call Center currently uses a legacy CRM system.  While the system is fully paid-for, it runs on hardware that is no longer supported by the vendor and the CRM itself is also out of support (though partial support can be obtained through a third-party).  Business operations depend on the predictable and reliable performance of the CRM.  Your business partner has sponsored a project to replace this legacy system.

Your business partner has been with the firm for some time and has been in multiple roles within the organization.  While not necessarily public knowledge, your business partner has been put in charge of this project as a ‘last chance’; should this project fail, part of the fallout may well be the elimination of your business partner’s job.  Therefore, in addition to needing a reliable CRM for Call Center operations support, your business partner also needs a win.

This is how the example above might look in the Greed/Fear matrix:

The ‘Professional’ column is usually the easy part.  An understanding of the business problem to be solved and the impact of doing nothing is generally enough, but it makes sense to gain a deeper understanding of the situation.  What happened in the past?  Why was the current system allowed to go so far out of support?  What drove that decision (or lack of a decision)?  These are all good questions to ask.  The goal is not necessarily to fill out a framework; the goal is to gain the necessary understanding of the ‘Professional’ wants/don’t wants involved in the issue so that you have a solid context around the issue itself.

The ‘Personal’ column is often times more critical than the ‘Professional’ and presents its own unique set of problems.  Most people at work want to look great and be successful in their job either because they want a promotion, want to get their full percentage of bonus or just because they get a deep personal satisfaction out of succeeding.  But most people aren’t likely to share their ‘Personal/Fear’ and asking them is likely to damage your relationship.

Your only hope in “populating” the ‘Personal/Fear’ quadrant is to rely on your ability to ask the right questions, listen effectively, empathize, and ultimately, to trust your instincts.  Some people are easier to read than others.  Other people will be more than happy to share the content of their ‘Personal/Fear’ quadrant (sometimes more than you want!).  Ultimately, you’re on your own to use your relationship-building skills to “populate” this key quadrant in the matrix.

You may also find similar challenges in “populating” the other quadrants.  People are not always as candid as you’d like with the ‘Professional’, either.  This is where the ability to build, maintain and leverage relationships becomes a key component in understanding the motivations of those with whom we work.  Don’t assume that you can simply ask about the ‘Professional’ and it shall be given.  You still need to sanity-check what you’ve heard against what you already know and what experience has taught you.  Trust your instincts.

Keep in mind that the intent is to use the matrix as a mental framework to understand the motivation and actions of others.  I don’t recommend telling others that you make use of this framework, as people may envision you analyzing them and writing down their motivations into little boxes.  I’d also recommend that you not share the “contents” of your matrix.  The purpose is to gain understanding so that you can communicate and work more effectively with others.  Branding yourself as a workplace arm-chair psychologist is not a brand that inspires trust and confidence.

© 2011, Mark E. Calabrese

Greed and Fear: Part I – Understanding the Framework

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In 2008, I had an interesting dinner conversation with a business partner, Vin Deschamps, CEO at Echopass.  Vin contends that humans are motivated by either “greed” or “fear” and I think he makes a valid point.  Thinking about that, it occurred to me that understanding these motivators from a personal and professional perspective could yield a simple, but effective leadership and communication framework.

Understanding the Framework

‘Greed’ is a loaded word with negative connotations, but at root, it’s wholly appropriate.  We may want more money, more free time to spend with our families, a new car, a better life for our children – any number of things – but ultimately we are motivated in part by what we WANT.

Conversely, we are also motivated by what we wish to AVOID – what we ‘Fear’.  We may fear losing our jobs, poor health, a downturn in the economy – again, any number of things – but we are similarly motivated by what we do NOT want.  If these observations don’t sound like rocket surgery to you so far, then we’re on the right track.

In the workplace, Greed and Fear come into play on two levels; the professional and the personal.  The Professional level revolves around the job or function we are paid to perform – completing project X, running your department efficiently, etc..  The Personal level revolves around your own goals for yourself – your personal brand, your career objectives, your clout, etc.

The matrix below shows how the framework might look:

The goal of the framework is to gain an understanding others, which is at the core of building, maintaining and leveraging mutually beneficial relationships.  Understanding people’s motivation (greed) and concerns (fear) at the personal and professional levels will help make sense of their words and actions, and how they interpret the words and actions of others.

The driver of the framework is genuine interest and the ability to listen and synthesize.  This means employing active listening and getting invested in the relationship.  You need to care about and have an interest in the other person.  You have to flesh out the framework with REAL content.

In Part II, we’ll talk more about how to use the framework, as well as its limitations.  As always, I welcome any comments either posted here or sent to me in email.

© 2011, Mark E. Calabrese

The Power of Indifference

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Preserving our sanity is an important part of being a leader.  Part of any good ‘Sanity Preservation Program involves understanding and properly embracing the ‘Power of Indifference’.  Let me start out by telling you what this is NOT.  The Power of Indifference does NOT mean being indifferent to the quality of our work, our team’s work, or our business partner’s and BT partner’s work.  Nor does it mean indifference to the consequences of our decisions, our partner’s decisions, our actions, the actions of others…hey, I could go on (and often do) but not now.

There is power, liberation and sanity in being able to “let go” and not let things bother you.  It’s only a job – it’s not life.  Just because work is part of your life (the part that provides the funding, anyway), doesn’t mean that work IS your life.  It’s not.  So don’t treat it as such.  You owe it to yourself to keep things in perspective and to preserve, protect and defend your sanity.

For most of us, almost nothing we do at work really matters.  Our work doesn’t end
war, doesn’t cure cancer and doesn’t make a better world for our children.  Some day in fact, all of our work will be thrown away and mocked by people who never even met us and life will go on.  Ultimately, there are only two things that matter at work:

  1. The relationships we build; and
  2. The deals we broker

Both of these help us grow as people and increase the value we can bring to our teams, each other and our partners.  So in the end, work is but the stage upon which we play out the drama of our careers – the value lies in your ability to keep things in perspective and to control events, rather than letting events control you.  When you are on the cusp of frustration, anger, or fury of the Russel Crowe or Mel Gibson variety, ask yourself this
question (and you have to ask it exactly like this):

“What difference does it REALLY make?”

Keep this in mind: Always be passionate about work; NEVER be emotional about work.

© 2011, Mark E. Calabrese

Five Questions to Ask Your New Team

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I originally read this in a WSJ article back in 2005.  The context is initial one-on-ones with your new team.  I’ve used these questions with much success and highly recommend them.  Make sure you ask them in the order below, as the first few questions will build some trust and ultimately should net you some good answers.  Make sure you listen and allow no distractions, but don’t take notes – that will only freak out your new directs.  An off-site meeting, like a lunch on you, is one good venue.  The questions are:

  1. What do you want to keep / stay the same?
  2. What do you want to see changed?
  3. What do you hope I’ll do?
  4. What are you afraid I’ll do?
  5. What questions do you have for me?

As with , any of my other posts, feel free to swipe as you see fit.  Good luck!

Keys to Effective One-on-One Meetings

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Here are some suggestions on making one-on-one meetings more effective:

  • Punctuality: Never, ever, ever be late – ever – regardless of who called the meeting.  This is not only courteous, but also indicative of your own reputation and core values.
  • Prepare: Always have an “agenda.”  Show up prepared, knowing what you expect to achieve.  What are your goals?  What do you WANT?  What do you NEED?  If you didn’t call the meeting, what does the OTHER person want/need?  Never just “show up.”  Every meeting, regardless of who called it, is a potential opportunity to further your or someone else’s agenda, so be prepared to ensure maximum return on both parties’ time investment.
  • Clarity: Be clear and up front about what you want to accomplish in the meeting, as well as understanding what the other party also wants to accomplish.  Clarify expectations, stay ‘on message’ and wrap up the meeting by making sure the goals were achieved.
  • Courtesy: If you expect a visitor or a call during the meeting, let the other party know up front.  Nothing says “you’re not that important” than taking a call or visitor during a one-on-one meeting so again – let the other person know if you are expecting a call or visitor that may require you to step away from the meeting.
  • Communicate: Make sure you listen and answer carefully.  You don’t have to always answer right away; if you feel pressured or need more information, let your guest know that you need to get further information but that you will follow up as soon as possible; verify your understanding of expectations or decisions – then deliver.
  • Candor: Be candid and to the point; no tap dancing.  Remember to use tact.  NEVER “handle” your customer or peer.  Go ugly early – if you have bad news, give it up….along with options, risks and recommendations.  Don’t leave the other person guessing as to what you wanted, what you were talking about and what the meeting was even supposed to be about.
  • Document: Verify any and all important decisions, expectation(s) or action items with a follow-up email (“Just to confirm what we discussed…”) or minutes (if it’s not overkill).  An undocumented meeting might as well have never happened.

None of this is really ground-breaking, let’s face it.  This is more a reminder of things we already know.  I hope these help!

© Mark E. Calabrese – 2011

The Three Roles of a Leader

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As leaders (in IT and otherwise), our job consists of three roles:

  • Identify new opportunities for the organization, team or group to add business value.  This involves building, maintaining and leveraging relationships with various stakeholders within the business and facilitating regular back and forth communication and dialogue between business operations resources and your own business technology resources.  As leaders, we are expected to be on the lookout for the team to ensure we identify opportunities and exploit them to our business partners’ best interests.
  • Remove obstacles and barriers to success.  This means either obtaining resources, facilitating discussions, or making a phone call to make a problem go away.  As leaders, we are the final point of escalation and our teams are counting on us to make problems go away.  We are expected to always be communicating and maintaining relationships that will enable us to be a resource to our teams when they encounter barriers to execution.
  • Preserve, Protect and Defend the teams’ culture.  This means ensuring that the team HAS an identifiable and USEABLE culture that is focused on execution, delivery and sound core values that resonate within the team and can be used not only to guide the team from a long-term strategic perspective, but from a day-to-day tactical perspective.  As leaders, we are expected to make the difficult decisions regarding resources – whether hiring, coaching or firing – to ensure that the team’s execution and delivery-focused culture remains intact.

By focusing on these three key activities, we not only serve our teams and their best interests in adding value to our business, but we also build and maintain a solid partnership with our business operations colleagues in helping them gain and keep a competitive edge.

© 2011 – Mark E. Calabrese