Project Management

3 Questions to Ask in Developing Your Technology Roadmap

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Maintaining a firm grasp of the basics is an essential element of being an effective leader.  This is especially true in developing a technology roadmap with your partners in business operations.  There are three basic questions to ask and answer:

  1. What do you HOPE will happen?: Leveraging technology to move the firm forward requires that your business partner have a vision of where to take the firm and how this vision impacts revenue, expenses, profits, etc.  As a leader, it is essential that you understand what your business partner “hopes will happen” so you can translate this vision into meaningful information and activities for your teams.  This way, your teams can apply the vision to their day to day work and become an active partner in the firm’s success.  Make sure you know the answer to this question and make it a part of your thinking, speaking and writing so that you and your teams remain focused.
  2. What are you AFRAID will happen?: Learn what your business partners fear and what those fears may cost.  Are the costs operational?  Financial?  Personal (reputation or career risk)?  Understanding the risk to business operations will help you avoid real costs and unnecessary expenditures.  Understanding personal risks will help you understand otherwise-mysterious behaviors on the part of your business partners.  Overall, you must ensure that you and your teams are aligned with the business in avoiding risk.  Your teams can further identify obstacles within their own ‘field of vision’ as technology specialists that may not be readily apparent to the business operations teams.
  3. What are you DOING about it?: Understanding how your business plans to achieve its goals and avoid risk is where you add value a solution provider and business partner.  This is where the collaboration between business and technology can pay real dividends in terms of cost avoidance, customer retention and revenue generation.  Active engagement between business operations and technology also provides opportunities to build a more collaborative culture within the firm.  Getting your teams to understand the business they support, the goals of that business and the risks that the business seeks to avoid can transform your technology team into a business technology team.  This means working to support the business’ plans but also leveraging the unique brain power of your teams to propose other opportunities to move the ball forward, all with a shared understanding of the firm’s goals and obstacles to success.  One team – one goal.

Knowing where the business is going, identifying obstacles on that journey and being aligned with business operations are the keys to developing strategies and tactics to remove barriers and achieve the firm’s vision.  Leaders must ensure that this knowledge drives innovation in three key operational areas for the technology teams:

  • Successful execution of one-time initiatives and projects
  • Implementing effective changes to day-to-day operational processes
  • Developing and implementing sound policy and procedures.

Ensuring that the activities in these three operational work streams are focused on achieving the ends of the technology strategy will significantly improve your teams’ focus and increase your effectiveness as a business partner.  Ask the questions – know the answers and make these answers meaningful in your teams’ day to day lives.

© 2014, Mark E. Calabrese

Just The Facts: Writing to Get Your Problem Resolved

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To get movement in resolving a problem, you’re probably going to have to write to someone.  Whether you’re trying to get justice from the airline or hotel who wronged you on your last business trip or if you need to reach out to a peer to clear a log jam that’s blocking your team, written communication is sometimes the best path forward.  Here’s a simple framework that I’ve found effective over the years for resolving personal and business issues:

  • What’s Wrong: Clearly and concisely state the problem. Keep it factual – not editorial.  No emotions and no speculating on someone else’s frame of mind.  Just the facts.
  • Impact to YOU: Be very specific and unemotional about how the problem impacts (or will impact) you or your team. Again, be concise and factual with no editorial comments.
  • Impact to the READER: Make it clear that you realize you may not be the only one impacted and that this isn’t 100% about you. How might the reader also be impacted?  Beware of sounding threatening; you probably won’t need to connect all the dots for the reader.  An overview of the “dots” is enough.
  • Propose a Solution: Never dump the problem on the reader, as he may well “solve” your problem but not in the way you’d hoped. This can leave you negotiating your way out of a solution that you asked for.  Instead, give the reader a quick and graceful exit by proposing a solution that can be accepted or countered.  Clarify how your proposal benefits all parties.  This way, you stand a better chance of getting the result that you want or at least negotiating something close enough.
  • Follow Up: Let the reader know when you plan to follow up, proposing a reasonable amount of time and then do so.
  • Respect: Be smart about cc’ing others if you’re trying to resolve a business issue. Ask yourself what impact this may have on the reader and on getting the results you want.  Will cc’ing others truly help or will it “give the reader something to think about?”  Don’t give them something to think about.  Get the problem solved.

I like to say that it’s always better to give someone a printed sheet and a red pen than a blank sheet and a black pen.  Applying this approach, along with some respect and common sense, should allow you to quickly solve your problem and move on.

© 2014, Mark E. Calabrese

Be Friendly – Not a Friend

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As a leader, you can be friendly with your team but you can’t be friends.  This is one of the hardest transitions to make as you move into a leadership role.  In the early part of your career, you’re “one of the guys” and that works when you’re a member of a team.  But you can’t be one of the guys once you are responsible for leading people.

First off, it’s awkward.  You’re no longer “one of the guys” and acting as though you are will only make people uncomfortable.  One of the guys can’t fire you or request that the project sponsor have you removed from the team.  Luckily, your best people probably don’t want you to be their friend – at least not while they work for you.  Strong teams want strong leaders – not best buddies.  A strong leader focuses on making smart decisions on the team’s behalf and not on making friends.  Unfortunately, your weaker players probably do want a best buddy, assuming that “friends won’t fire friends.”

Not being friends doesn’t mean you have to be a cold, calculating automaton.  Leadership is about influence, which is earned by everything you do, say or write.  Being friendly is a leadership style and while it doesn’t mean kissing up to your team, it does mean being a decent human being and maintaining a positive, open attitude.  It’s easier to earn influence if you’re friendly and approachable.

Being friendly is a good way to put your team at ease and to foster open and regular communication – the lifeblood of any good functioning team.  This also sets a positive example for your team on how to relate to other people.  A team that regularly earns influence within an organization will strengthen their ability to execute and get things done.  This is a key cultural goal for any leader in building an effective team.

Being friends with people on your team gives the appearance of favoritism and may alienate some of your more effective resources.  Instead, seek to earn your team’s respect by setting a good example and by being friendly and open to their ideas.  You’ll be surprised how forgoing friendship while working with your team will often result in true friendships after your professional relationship has changed….and I’m speaking from personal experience.

© 2014, Mark E. Calabrese

How To Make an Enemy of Your Project Manager

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Worst Nightmare

So you’ve decided to make an enemy of your project manager.  You’ll be surprised at how little effort will be required on your part to achieve your goal.  Here are four easy steps to quickly reduce your value to your team and your PM: 

  1. Silence: Never let your project manager know if you see any risk in making a deliverable date (particularly if your deliverable is on the critical or one of the controlling paths).  Things might clear up on their own and let’s face it, the project manager will just get mad if you tell her.  Also, don’t bother yourself with informing the owners of any predecessor or successor tasks of the risk as this will only make you look bad.  The less you say, the better.
  2. Task Information: If you break radio silence, don’t let your project manager know which task or deliverables will be impacted.  If you’re using a project plan, don’t provide task IDs or any other information that might help the project manager track the risk back to specific work-streams in the plan.  Giving your PM this information will only result in his going off to model the potential impact of the delay and start taking mitigation actions.  Better to be vague and maybe tell a few other team members and let things “trickle up” to the project manager on their own (PMs know everything, anyway).
  3. Estimates: If you go soft on providing task information, avoid providing estimates of how significant the delay might be.  This will only allow the project manager to model the impact, set expectations with project sponsors and take mitigation steps to keep the project on track.  And let’s face it, you’ll be held accountable for your estimates.  This smacks of the injustice of team members getting blamed for everything they do.
  4. Thought Leadership: Ultimately, the key to making an enemy out of your project manager is to provide absolutely zero thought leadership on mitigating or avoiding any impact to the project plan.  Don’t get creative and provide ideas.  Try “thinking for management” by filtering out any idea that you are “absolutely certain will be rejected” or that might make you look bad by appearing to question management.  As with estimates, your idea might be implemented and if it doesn’t work out, you could be held accountable.  The smart move is to sit tight and wait for someone to tell you what to do. Remember – inaction is action when it comes to making enemies on your project.

By following these four easy steps, you will not only alienate your project manager but also position your team for failure.  Communication, accountability and planning can be stressful and who knows – you may even prove to be an example for other who want to avoid this type of stress.  Only by failing to lead can you ever hope to lead others to failure.  Good luck!

© 2014, Mark E. Calabrese

Present & Reporting or DRIVING & LEADING?

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Projects don’t fail due to lack of process – projects fail due to lack of leadership.  That said, there are two approaches to project management; “present & reporting” and “driving & leading”:

Present & Reporting: Far too many project leaders take the ‘present & reporting’ approach.  Geared more toward the administrative side of the discipline, this approach focuses on form and function.  Minutes are carefully taken and the project plan is meticulously maintained.  Risks are delineated, Issues documents and project artifacts are developed and socialized.  While these elements of project control are critical to success, they are not the true calling of the effective leader.

It’s not enough for the project leader to know what’s going on and to report events.  This is more the role of a project administrator or project coordinator – a supporting role in the overall endeavor.  The elements of ‘present and reporting’ are solid risk management tools, ensuring that team performance never falls below an established minimum but they do little to ensure the team attains maximum performance levels.

Driving and Leading: Motivating and influencing your team to achieve its maximum potential requires the ‘driving & leading’ approach.  This demands that the project leader live and breathe her project.  You might think of this as the ‘project Geek approach’ and that’s not a bad way to think about it.  The effective project leader is constantly thinking, talking and acting in the project’s best interests, looking ahead and seeking out opportunities for the team to succeed while also removing obstacles to that success.

An effective project leader must maintain a sense of urgency on the project, constantly seeking ways to communicate to the team and motivate them to action, while not bombarding them with emails, process and administrivia.  This is not an easy balancing act and requires focus, clarity in communications, soliciting and heeding feedback, and evangelizing about the goals of the project.  Most importantly, it requires the project leader to set the bar high by setting a good example for the entire team.

The effective project leader doesn’t need to know everything about the project; rather, the effective project leader needs to know everything about how to get things DONE on the project and how best to keep the team motivated, informed, focused and executing on a daily basis.

© 2014, Mark E. Calabrese

Project Status Reporting – A Radical (?) Approach

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Business sponsors know what they are “expected to expect” from a project status report.  Likewise, most project managers know what is “supposed to be” in a status report.  While much of this standard information is relevant, oftentimes status reports can be less about “information I need to do my job” and more about “information that, by God, is just supposed to be in a project status report!” (optional ‘harrumph’).  We don’t produce status reports to satisfy the Gods of Project Management; we produce status reports to communicate information relevant to the business sponsor.

With that in mind, I’m going to propose something radical here.  Rather than start with a template approach, I’m going to propose that the project manager sit down with the business sponsor and ask a few simple questions, such as:

  • After you read the status report, what do you need to be able to do?
  • What information do you need at your fingertips to effectively communicate with your peers and your own management?
  • Help me understand how you are going to use this data.
  • What do you need to be able to do AFTER you read the status report that you simply cannot do BEFORE?
  • What are your major concerns about the project from a business perspective?

You get the idea.  Your goal is to understand your specific desired outcomes your business sponsor may need to engineer using the data in the status report.  You also want to understand what information she needs in order to do her job and how she will use this information.  In a word, you want to understand what she needs in order for her to be successful.

One size fits all isn’t necessarily the best approach and long, busy status report may end up providing lots of data that is of no use to your business sponsor.  The result is extra work for you, status reports that aren’t always read (resulting in frustration for the project manager and the team) and ultimately, poor transparency and communications from the project up to the business sponsor.  A good status report is lean, clean and content-rich making it a quick read and a powerful, complete and effective tool to communicate key data points your business sponsor needs.

So my radical proposal is simply this – identify and keep the end goal in mind before you determine the best way to communicate status toward achieving that end goal.  This way, you can make effective use of both your and your business sponsor’s time in communicating status while significantly improving the chances of your mutual success.

© 2013, Mark E. Calabrese

Transparency – Applying the ‘Price Tag Approach’

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A valuable guiding principle in business (particularly in technology) is to never “protect” your business partners from the consequences of their decisions.

I’m a big believer in what I’ll call the “price tag” approach and it goes something like this.  Suppose you’re a sales associate at the local Jaguar dealership.  If your customer is a first-time Jaguar buyer, it’s probably a good idea to explain that purchasing a Jaguar loaded up with options is also a purchase of more expensive service calls, oil changes, repairs and of course an increased risk that some kid will snap the cat off your hood.  This way, 3,000 miles later, you don’t have an angry customer complaining about the $100 oil change he just paid for.  All you’re doing is setting expectations by helping your customer understand the consequences of his decision – something he may not know and may not ask.

Too often we assume that upper management already knows and understands all the implications of their decisions and requests.  After all, they ARE management.  However, this is almost never the case.  Management relies on the thought leadership of their teams to ensure that they have every opportunity to never make a bad business decision.  Therefore, consider applying the principles below in establishing your own strong brand of transparency within your firm:

  • Understand The Request: Fully understanding the request itself isn’t enough.  More important is understanding the desired business outcome of the request.  Your CIO wants X, but for what purpose?  WHY does she want X?  Understand the business problem that needs to be solved and not just the specifics of the tactical request.
  • Understand and Surface ALL Costs: This includes not simply the financial costs but also the impacts to other initiatives and stakeholders.  While the request may come from your CIO, there may be implications that span a broader area than the CIO’s scope of responsibility.  Think in terms of impact to the business, holistically and not simply within your silo.
  • Identify Risks: Make sure you identify and clearly communicate any risks associated with fulfilling the request, providing mitigation or avoidance options where available.
  • Document & Deliver Options: With the desired business outcome in mind, communicate what options are available, listing pros and cons for each and documenting them in a brief but clear email with all appropriate stakeholders cc’d.  Include risks and mitigation/avoidance strategies.
  • Make A Recommendation: Always deliver such information with a recommendation by you and your team.  Dumping a problem on the bosses desk is bad.  Delivering a problem with options is better.  Informing your boss of the options and making a recommendation is optimal.  What do you recommend your boss do and why?  Help make her successful.
  • Follow Up: Respectfully and reasonably follow up to ensure a decision is made, that the “full price tag” is understood and accepted, DOCUMENT THE FINAL DECISION and then execute.

Transparency is a great buzz word that we all like to use – me included.  However, transparency is a two-way street.  Applying the ‘price tag’ approach to transparency will help ensure that you and your teams provide your boss and your business partners the valuable opportunity to never make a bad decision.

© 2013, Mark E. Calabrese