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!

Technology-Imposed Hiatus

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Apologies to anyone following my blog, wondering why there haven’t been any recent posts.  My motherboard died on my Sony Vaio.  I took my laptop to Abt (for those of you who don’t live in Chicago, Abt is the electronics toy store for adults – let’s face it, it’s mostly for guys, as we like things that plug in, light up and make noise), as I have an extended service contract with them.  At first they told me they’d put a 2-day rush on the part.  Then a few days later they told me it would be 7-10 days.  THEN they told me it would be a few more days.  THEN they told me they’d give me a loaner….then I found out that they had receive the motherboard and installed it…..but that the keyboard and mousepad were also fried and that those parts were on order.

Mind you, this all transpired over two weeks and one day.  I’m starting my third week with no laptop, but through the generosity of a good friend, I finally have a loaner.  I’ll be calling Abt later today to find out if the parts will REALLY be in on Tuesday and if I’ll get my laptop back on Wednesday.  In the meantime, I’ll be using this very nice temporary laptop, which is far, far better than typing up all my emails on my Blackberry using my thumbs.

HAT TIP: To Art Hopkins and Steven Getto for the spell check on ‘hiatus’!

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

“Business Agility” by Mike Hugos

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I’m currently reading Mike HugosBusiness Agility.  I met Mike at a Technology Executive Network (TEN) meeting in Chicago late last year.  The point of the book is to introduce the idea of applying Agility principles to the business world and not just to software development.  Mike makes a good case as to how this can be done but more importantly, he points out WHY it makes sense – especially given how quickly companies must adapt to ever-changing customer needs.  I’m not finished with the book yet, but I think it’s worth the read.

Mike is a very interesting guy, who bills himself as a ‘CIO at Large’ and runs the Center For Systems Innovation (c4si).  We’ve had a few discussions (somewhat convenient that he just lives a few blocks down the street from me) and I have to say that I’m glad I met him.  I owe Phil McEntee, who runs TEN, a ‘thank you’ for the connection.

You can read Mike’s blog here.  Mike also write and blogs at CIO Magazine and Computerworld.



Getting Your Team To Develop Goals Aligned With Your Strategy

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We’ve all seen this before.  We ask our teams to develop individual goals that are aligned to corporate strategy, but we find that our teams are trying to force-fit their own personal goals (read: things they want to do, irrespective of corporate strategy) into the strategy framework.  In other words, if you have a team member who really wants to take a Java class, but there’s no link to that objective and to achieving the desired technology component to the corporate strategy, you need to get that team member aligned appropriately while still helping them achieve their own goals in the context of business operations.

This is symptomatic of our not providing clear leadership, tying strategic goals back to regular day-to-day tactical life; basically showing how real work RIGHT NOW is tied to strategic goals.  Try this framework on for size and see if it works for you.  It’s a take (maybe?) on the ‘Three Step Plan’, though I have to confess that apart from Andy Willoughby’s website, which is pretty much content-free, I still have no idea what the ‘3 Step Plan’ really is:

ONE Message – Evangelize!: Once you’ve rolled out the strategic roadmap, giving the presentation, handing out t-shirts and the like, you need to be an evangelist for the roadmap on a DAILY BASIS.  That means that you seek to put most events, work, issues and opportunities within the framework of the roadmap.  If the business strategy changes, so should the roadmap as well as the gospel you’re preaching.  The aim here is to get your team to understand that: 1.) the roadmap is REAL and it isn’t going anywhere’ 2.) that the roadmap is a regular topic of conversation, as it has a strong relationship to every day real work; and 3.) that you take it seriously.

TWO Questions to Ask: Ask these two questions about every goal proposed by your team: 1.) What business problem will this solve?; and 2.) How will things be different tomorrow after you’ve achieved this goal?

THREE Workstreams: There are three workstreams in business technology in which the strategy needs to be realized in the form of tactical objectives and individual goals:  1.) Day to Day Production Support and Issue Resolution or ‘Lights On’; 2.) Projects and Initiatives or ‘New Development’; and 3.) Policy and Procedures.  There is no ‘fourth workstream’ called ‘Strategy’.  Any strategy must be executed in one of these three workstreams.  Make sure your teams understand this and that they develop their tactical objectives within this framework.

One last word on measurement.  Ask each team member to define the OBJECTIVE measure by which they’ll know that their goal was attained.  The key here is ‘objective’ and I use the following example to make the point.

Your team member should choose a measure that, if you (the boss) were to be hit by a bus the week before reviews are due, that there would be NO QUESTION as to whether the goal was achieved or not.  No one can argue that 2+2 doesn’t equal 4; it’s another matter if you’re stating that you’re going to do a “really great job” at something.  Quantify it where you can and leave no mistake as to whether the goal was achieved.

In an upcoming post, I’ll talk about developing strategic roadmaps and tying them to actual day-to-day life for your teams.  As always, comments and emails on this and other posts are always appreciated!

© 2011 – Mark E. Calabrese

Automating PMO Workflow

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Lately, I’ve noticed that a lot of organizations are seriously considering purchasing tools to automate their PMO workflow.  While there are certainly some good products out there worth considering, I think it’s important to avoid the “rush to automation” as a solution to all problems.  Automation doesn’t solve every problem, so it’s always a good idea to initially approach the problem using a version of the following framework BEFORE committing company resources to the purchase, installation and integration of a PMO or project workflow tool:

  • Understand the Current State: Clearly define the current project workflow.  Make sure you not only document and understand the PUBLISHED workflow, but how it actually works in practice.  If there’s a gap between the processes and practices in the current state, things will only get more complicated as you try to move to a defined future state.
  • Understand, Clarify and Document the Future State: Make sure that the desired future state is clearly understood and documented.  This will become important when you sell the idea internally, as well as when you begin to gather and document requirements.  Make sure that there is agreement on the future state among all stakeholders – business AND technology.  EVERYONE has to agree on what “tomorrow” looks like or you’ll be setting yourself up for another host of interesting complications.
  • Gap Analysis – Part I: Perform a gap analysis of the Current and Future states and DOCUMENT WHAT YOU FIND.  This will serve two purposes, as I’ll point out below.
  • Analyze and Improve the Current State Workflow: Before building out your requirements, looking up and talking to vendors or scheduling demos, stop for a moment and determine whether your existing workflow is optimal.  Can some of the problems be resolved by simply improving the existing workflow and avoiding the expense of finding and implementing an automated solution?  As advisors to our business partners on how they invest their IT dollars, it is incumbent upon us to make sure that the PMO workflow we intend to automate is optimal in the CURRENT STATE.  Avoid the idea that “we’ll improve the workflow when we implement the new solution”.  You may find that optimizing the current solution will be enough to meet the business’ needs.
  • Implement the Improvements: Once you’ve identified ways to optimize the existing workflow, implement the changes.  Make sure you’ve captured any metrics as a baseline so that you can test the improvements to see if they deliver the desired changes.  If they do, then you’ve resolved a business operations issue at minimal cost.  If the changes do NOT yield the desired results, at minimum you’ve not only improved the existing process that will be automated, but you’ve shown your business partners that you treat their IT investment as YOUR investment, too.
  • Gap Analysis – Part II: Now that you’ve optimized the existing workflow, perform the gap analysis between the new and improved Current State with the Future State.  This should result in a set of RFP-ready requirements that can be used in vendor selection and as a basis for the implementation and integration effort.

Remember that as IT leaders, our mission is to deliver products and services that meet or exceed our partner’s business needs and to ensure that we advise them such that they NEVER waste their IT investment.

© 2011 – Mark E. Calabrese

The Next Change In IT Leadership….Are You Ready?

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Hello and welcome to my blog.  My purpose in writing this blog is to explore the changes in our industry and how such  changes will impact us including how we must change ourselves, our teams, how we interact with our business partners and how we manage our careers.  I’m hoping that I can share some of my observations, getting some good feedback in the process and also create a friendly forum for other authors and readers to share their thoughts.
My focus will be on IT strategy in the business environment, including how we introduce, implement and manage change (both operational and cultural), how we organize our teams, how we execute our work, deliver services and partner with the business.  This is my first forray into the blogosphere, so bear with me as I figure out how to get the blog set up and looking presentable.  Enjoy your visit and thanks for stopping by!


Much has changed in the world of information technology and the changes show no signs of slowing.  In recent years we’ve seen a very quiet but significant change in thinking about IT leadership.  Where at one time, a strong technical background in application development or infrastructure was a non-negotiable prerequisite, more recently the trend has been toward a focus on business knowledge.  I expect this will only continue.

Part of this trend is based on the business’ desire to control costs.  C level executives in IT are expensive – less so Director level management.  Where at one time, CIOs and CTOs reported directly to the CEO, more and more technology leaders are again reporting to COOs and CFOs, causing many to question the need for C level technology executives at all.
Another part of this trend comes from the maturation of our workforce.  With much of the workforce already having a basic technology background (and increasingly more than just a basic understanding of IT), the mystery around understanding technology is seen less as a challenge requiring a highly paid former-geek and more an opportunity to recruit someone with strong business knowledge and a working appreciation of technology, such that this knowledge can be leveraged to improve business operations and drive revenue.
Technology is being seen less and less as a separate and distinct expense that one must incur and instead is being seen as a business investment from which management expects a return.  This paradigm shift not only impacts how business and technology interact, but also will require a change in the type of leadership required.  IT leaders will be seen less as technologists who work with the business, but as business leaders who specialize in technology.
The essence of this change is the shift from ‘information technology’ to ‘business technology‘.  More than semantics, this change in mindset requires technology leaders to think of themselves as business resources first and foremost.  The ability to understand the connection between business operations and revenue retention and growth and to leverage this knowledge in developing and executing strategic roadmaps is where the value of the future IT leader lies.
This said, the need for IT leaders to both understand and embrace this change is essential.  As we come out of the Great Recession, I expect we’ll see a major shift in IT leadership and management across all industries.  We as technology leaders must be able to successfully navigate this change, understanding what it means to us today, tomorrow and how we’ll adapt.
Change has always been the essence of IT.  Unfortunately, people are not hard-wired to embrace change.  We like things very predictable and systematic.  Since we’ve chosen this industry, it is incumbent upon us to first manage ourselves and our own resistance to change, then as leaders, help our teams navigate the ever-changing landscape of technology.
In the months ahead, I hope to delve deeper into some aspects of what we do, how we do it and how we can be effective.  Comments are ALWAYS welcome and patience, as I get better at this, is definitely appreciated!

Feedback: Giving and Getting

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Ask anyone if they like getting feedback and they’ll almost certainly say ‘yes’. However, fewer people like giving feedback as that’s a potential minefield.  Since most feedback doesn’t fall into the “you’re really great” category, consider the following when giving feedback:

  • Timing: It’s important to deliver feedback in a timely fashion, particularly if it’s around a specific incident. The more time that passes, the harder it will be to effectively give feedback. If you wait, what will you say when you’re asked, “Why did you wait so long to tell me?” You also want to give feedback while the events and details are fresh in both your and the recipients mind.
  • Prepare: Take time prepare before you give feedback. This is especially important if the feedback is ‘negative’ and if the recipient may not take the feedback as intended. Know what you’re going to say in advance, how it may be taken and how you will respond.
  • Audience: Be conscious of how you phrase your feedback – packaging is everything. While you don’t want your feedback watered down like a Happy Hour drink, successful feedback requires considering the feelings and disposition of the receiver. Will they understand what you mean and what your intentions are?  Are your words “loaded” or “negative”? Are you being too vague? Remember – you’re selling someone your observations on how they can be more successful – make sure you package your message well and that the packaging allows the consumer to see what’s inside. Ask yourself, “Is what I am about to say REALLY likely to give me the result I want?”
  • Motivation: Why are you giving the feedback? Is it out of a genuine interest in someone else’s success or are you frustrated by their behavior on some level? Giving feedback out of frustration or a desire to “give someone something to think about” will backfire in almost all cases. Make sure you are coming from a good place and that your motivation is beyond reproach.
  • Brevity: You will probably be telling someone something that will be hard to hear, so be brief, clear and to the point. Repeating the feedback over and over can
    backfire, so phrase your feedback well and deliver it once. In almost all cases, if you’re clear and brief, the feedback will be understood on the first pass.
  • Moving On: Once you’ve given the feedback, don’t dwell on it, don’t apologize, over-explain, etc.; just move on. If the recipient approaches you and asks for further feedback, then do so cautiously. This probably isn’t a request for you to completely unload, so consider that while it’s difficult to hear negative feedback, its more difficult to ask for more. Don’t be the one to “follow up” with them at a later date.

While giving feedback isn’t always easy, getting feedback can be tough, too.  Why?  Because it’s about YOU.  It’s tough to hear something that runs contrary to your image of yourself.  Hell, I’m no different.  But learning how to GET feedback is essential to your continued success in building your brand, improving your performance and growing as a human being.  A few tips:

What You Should NOT Do:

  • Get Defensive: Listen through the pain and hear what the speaker is telling you.  While you may not agree, the fact is that THIS IS WHAT IS BEING PERCEIVED and if one person sees it, others probably do, too.  I’d say “don’t take it personally” but it’s kind of hard when the feedback is about you.  We teach people how to treat us and if you teach people that we don’t take well-intentioned feedback well, then people will stop trying to help you.
  • Explain: This is a HUGE mistake and is a corollary of the above.  Explaining tells the speaker “it’s not me, it’s you – if I can just straighten you out (as well as the rest of the world), then I can go back to what I was doing before you came and
    offered me your precious feedback.” This is a great way to indirectly tell someone who they don’t know what they’re talking about.  They may well BE wrong, but the fact remains that this is their perception and it’s likely that others perceive the same thing.  Remember – it’s hard enough to give feedback. Don’t make it harder by showing people they’re wasting their time in taking a chance on you.
  • Interrupt: Another great way to say “Talk to the hand, cuz the face ain’t listening” (most effective in the Ali G accent) is to cut off the speaker.  Listen
    through the pain and deal with it.  Interrupting may well stop the flow of potentially valuable information.  Shut up and take it in.
  • Judge: Even if the feedback is poorly or even rudely given, listen.  Even an idiot can provide valuable information.  Withhold your judgment – get the feedback while it’s hot.

What You SHOULD Do:

  • Listen: Take it all in, even if you dislike or disagree what you’re hearing.
  • Keep Your Poker Face: Even if it hurts, you can’t show it.  Why?  The speaker may be quite stressed, giving you feedback that isn’t positive.  Be conscious of your body language and nonverbal queues.  Your aim is to keep the information flowing and to make the speaker “feel safe”.
  • Reflect: Even if the feedback is poorly given, do they have a point?  Might they be right?  Think about it – ask a “trusted advisor” or significant other if you have to.
  • Get Cool With It: Talking to your friends, peers, trusted advisors or significant other will help you get past hearing bad feedback so you can figure out how you’re going to change your behavior and apply what you’ve heard.  No need to go it alone – reach out to those around you.  You’ll find more solace than you realize if you can allow yourself to be vulnerable.

You can’t escape the fact that you’re going to have to give and get feedback in your role as a leader and as a team member.  Make sure you’re head is in the best place to make the most of feedback, whether its coming FROM you or TO you.

© 2011 – Mark E. Calabrese