Comfortably Numb


Count the number of times per day you encounter the following:

That’s the way we’ve always done it.

It is what it is.

We can try, but it won’t do any good.

Those words you’re hearing? That’s surrender.

The only proven way I’ve found to counter surrender, is through a series of wins.

Small successes at first, to be sure… but building up to bigger and bigger victories, as people learn to trust in your ability to deliver.

Doing what you say you will do. On time. On budget.

The old saying goes “nothing breeds success, like success.”

What this really means is that people gain confidence, through seeing performance and achievement occur, right before their very eyes.

So – when you encounter an environment where skepticism is the norm, and pessimism is the standard operating procedure, come in with a goal of attaining one small success in the first two weeks. Another goal of attaining a bigger success in the first thirty days. Still another goal that is larger still, to be achieved in the first ninety days.

Success will breed success, and you will win people over.

The key objective is to change the dialog, from defeatism to optimism, by building one success atop the other.

Don’t say trust me. Don’t challenge the status quo day one.

Meet people where they are. Show them a pathway to success.

And then, lead them there, one win at a time.

Go, and be you.


100 Things You Are Doing Wrong on Social Media | Oracle Marketing Cloud

Doing it Wrong

100 Things You Are Doing Wrong on Social Media

via 100 Things You Are Doing Wrong on Social Media | Oracle Marketing Cloud.

Choking on an Elephant


This morning, I was going to riff on some tired tripe about “eating an elephant… one bite at a time.”

And then realized: I would hate reading something like that.


Even so, tackling seemingly unassailable – and impossible-seeming – projects has been very much top of mind for me these days. And honestly, it is making me put my best problem solving, King Solomon decision making skillz to the test.

Without falling back into tired homilies, then – how does one begin managing the unmanageable?

Identify the “big problem.” First, you must understand the big problem needing to be solved. Surprisingly, many projects go off the rails at this very step. Correctly identifying what the big problem to be solved is, and keeping it at the center of every conversation in the project, is vital to having a successful outcome on the other end of the process.

Break the big problem down. Once you identify the “big problem”, begin deconstructing the process by which you will obtain a solution. Draw pictures. Paste stickies to the wall. Create user personas and user stories. Create tasks that are understood by the team, and make sure everyone on the team understands how each task leads to the completion of the big problem.

Assign responsibility. Once the big problem has been deconstructed into manageable chunks, the next step is to assign responsibility to the oversight of each element in the process. Maybe it’s a project lead, or engagement manager. Perhaps it’s even a user. Someone, or a collective group of someones, must ultimately be accountable to each element of work.

Set milestones. As travelers, we know where we are, by the milestones we pass along the way. The same is true of our projects. Milestones are those events in the life of projects, by which we gauge our progress – or the lack thereof. Defining milestones is not a passive activity – it requires careful thought and communication, and may not be strictly defined by individual sub-projects within the project. It might be when “minimal viable product” is reached. Or, when you can invoice for the next payment. Whatever your milestones are, they should be broadly visible, universally understood, and tied directly back to those held responsible (see previous paragraph).

Monitor progress. If you adhere to an Agile development process, you monitor your progress through your scrums and by what is accomplished through each run. If you are less formal, perhaps you simply check in with your team on a regular basis. Whatever your style, methodology, or philosophy, you need some form of continuous feedback to let you know where you are. And by monitor, I don’t mean show up when a milestone is supposed to be complete, and expect everything to be hunky-dory. Be engaged. Be attentive. Be proactive.

Adjust as needed. This is a natural consequence of monitoring progress. Because – surprise, surprise – all our well laid plans have to exist in the real world, where vacations, life, unforeseen events, and plain old human frailty conspire to bring our projects to a screeching halt. You need to be flexible, and make mid-game adjustments, if you ever want to foster your behemoth project to a successful end.

Now, your mileage will definitely vary. And, if you’re fortunate enough, you will live through many iterations of current management style, speak, and methodologies throughout the course of your career.

What your project management success will ultimately boil down to, is mastering how to go about solving “intractable problems”, regardless of the fact-dependent and unique circumstances of each individual project – and applying those lessons learned from each engagement, toward the betterment of the next project you encounter.

Go, and be you.


When to Be Strategic

Strategy 2

In due course of any given day, we are busy at work, knocking off the tasks on our to-do lists.

Yet, rarely do we stop and ask: Am I working on the right problem?

This is not meant to be a trivial or flippant observation. We may be very hard at work, and producing copious volumes of output.

But – are we actually doing the proper things that need to be done, or merely, those that are the most expedient? Are we cognizant of the Strategic, as well as the Tactical?

Why is this important?

Because everything you do in your organization begins – and ends – with your strategic initiatives. Every conversation. Every decision. Every assignment. Every project.

It is the superstructure that gives shape to your culture, to your management, and to your financial planning.

And yet – we are continually swamped with the immediate, with the needful now. We are daily disintermediated by the crisis of the hour – which leeches and robs us of our drive, focus, and energy needed to accomplish our ultimate goals and targets.

So – how do we keep the main thing, the main thing?

  • By communicating to our colleagues and direct reports, explicitly, our strategic initiatives;
  • By daily discriminating between what is tactically within our strategic objectives, and removing anything that detracts from our core mission;
  • And by constantly monitoring our activities, to insure we are holding true to our strategic plan.

Organizational politics, economics, and unforeseen crises will test your resolve.

It is incumbent upon you as a leader, manager, and educator to keep strategy front and center – at the water cooler, in the board room, and in the classroom.

Go, and be you.


He’s Pining for the Fjords

Pining for the Fjords

Q: When is a technology dead?

A: When you can pry it from your user’s cold, lifeless hands.

Now: it probably isn’t that bad at your school. Or, maybe it is.

I spent the better part of the day today going through boxes and boxes of old IT gunk – everything from SCSI II cables, to Centronix Printer Cables, to Bubble Readers.

Conversing with someone who is fighting tooth and nail to keep his blackboard and chalk. Gently coaxing another who is unshakable in their belief that we should continue replicating hundreds of CD-ROMs, rather than uploading one copy of our video to the cloud. Discussing why we need to keep stringing VGA and sound cables to our smartboards and projectors, rather than implementing a single cable HDMI solution.

Hundreds of small battles fought per day. Wondering if the war can truly be won.

The simple fact is: we are all comfortable with a certain baseline of technology, and our ability to wield it effectively in the classroom, or in the boardroom.

Beyond that: someone may have to die, in order for change to truly take hold.

Pining for the Fjords

So. We can boldly declare obsolete technologies to be Dead. Deceased. Gone to meet their maker. Singing with the Choir Eternal.

Pining for the Fjords.

Or – we can pragmatically realize that we must meet our teachers and staff where they are in their technological mastery, and focus instead on the goals of our teaching and instruction, rather than the uniformity and currency of our technology platforms.

Go, and be you.

Smartphone Survival Kit

Survival Kit

There are many, many realizations that arise, as one moves from a city of 50,000, to a city of 10,000,000.

One is that having a smartphone is not merely optional. It’s a requirement.

Directions. Train schedules. Nearby restaurants. Subway routes. Cabs. Your smartphone is your modern day survival kit for living in the big city.

Here are the most commonly used “tools” in my mobile survival toolkit:

Google Maps – the most used app on my phone. Invaluable for locating the nearest subway station, best route to get from point A to point B, and for just simply finding out where in the heck I am.

Uber – while the mark of a true urbanite is their mojo in hailing a cab, with Uber even a n00b can get around anywhere in the big city… for a price, natch. Sometimes very pricey during “surge pricing”, there is still no better way of getting door-to-door in the City. Uber is a close second in my list of “must haves” in your survival kit.

MyTix – if you grab the train from Garden State, the New Jersey Transit mobile app MyTix is an absolute must have. Makes it super easy to buy, and store your train tickets. Plus, when you pay a $5 premium for buying your ticket (cash only) on the train, it can be a lifesaver (just make sure to keep your phone charged). Which leads me to…

Charger – my iPhone 5S battery is totally shot. Which means that by the time I ride the Q train from Herald Square to Avenue J, there’s more than a fair chance that my battery is well on it’s way to being dead. That’s why I always carry a spare charger, to plug in where, and when, I can. (Yeah, yeah. I need a new phone. Soon.)

So – What did I miss?

Tell me your essential smartphone survival tips, in the comments below.

Go, and be you.

Road Trip

Road Trip, Man Plans, G-d Laughs, 300 Words 2 Minutes

Man Plans, G-d Laughs

I began my road trip today – a drive across half the country, from Arkansas to New York City.

I don’t have to tell ya’ – Flatbush ain’t Conway.

This is the third – or perhaps the fourth? – time, that my family and I have loaded a truck, and criss-crossed hundreds of miles to a new home, a new job, and a new set of friends.

You know – it isn’t for the faint of heart. It’s challenging. It’s scary. It’s – literally – life changing.

Five years ago, I didn’t envision being a CIO at a top liberal arts college. Last year, I wasn’t thinking about being the Director of IT at a large independent school in the middle of Flatbush, Brooklyn.

Where will you and I be five years from now? Who’s to say? Man Plans, and G-d Laughs.

I’m very grateful that my new colleagues have been welcoming, generous, and kind.

And, happily, the only faux pas that I’ve been directly challenged on were (1) ordering sweet tea, and (2) misspelling the name of my new employer. Oy.

How far, and how fast, will the remainder of the journey be? I’m ready to find out.

Open the door. Step on the road. Embrace the journey.

Go, and be you.