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Asking the Right Questions

By TJ Johnson posted 12-19-2018 21:07

  

I’ve always been known as the “What About?” person. Through my days as IT Director of a law firm, managing the law department of a global life insurance company, working with many IT Leaders across the legal industry in my work at ILTA, and now as legal strategist at an IT services and consulting firm (Olenick), I’ve been the one asking “Why?” and “Why Not?” Being inquisitive has helped me fill in context and lead successful, creative problem-solving projects. I’ve honed my provocative questioning skills over time, and now I share ideas on how to ask the right questions, at the right time, of the right people, and in doing so, help lead your legal organization into a successful future.

“What are the most pressing business challenges in legal organizations today?” “Do your current IT projects leverage technology to address those business challenges?” Two loaded questions without simple answers, but they need to be asked. Here are a few more questions:

  • Do you know what your legal organization’s fundamental business challenges are?
  • Do you know how many IT projects are somewhere in the planning cycle in your organization right now? 10? 100?
  • Of those you know about, can you point to documentation of the business challenge each addresses?
  • Is the business challenge being addressed something the IT department defined or is it a fundamental business challenge of the firm, as outlined by management?
  • Can you articulate project goals in the language of managing partners?
  • Can you articulate the ways you will measure success of that project, not only from the perspective of the technology itself but in how it will integrate successfully with other technologies, the tests it has to pass during each phase of the project, how it will be accepted and adopted by the users, etc.
  • How risk averse is your organization? What is the tolerance for failure?
  • And, is the project trendy? Does it have the word “innovative” or “AI” or “blockchain” or “app” in it?

Feeling comfortable now? What do you think managing partners list as 2018-19 business challenges? Here are a few:

  • The fragmentation of the legal market and the decline of the institutional relationship with clients, consolidation
  • Competition, downward rate pressure, overcapacity, profitability
  • The ability to differentiate legal service offerings and digitally transform operations to ensure using people, data, processes and technology to deliver the best client experience
  • Staying at the forefront of the regulatory landscape

How do you match those to your IT Projects? Not too hard for an AI project or security awareness program, but not as easy for Windows 10 upgrades or moving to infrastructure as a service. Sometimes it’s a case of just being brutally honest and asking a choice question - “Which option should we go with: do the upgrade so we continue to have a solid infrastructure to build on, or turn that work over to other people to take care of, so we can focus on the projects that directly address our business challenges?” Either way, you want to ensure you have that base to build your strategic projects on; that’s where you provide the most value.

Back to what business challenge your IT project is addressing. Think of it as a puzzle where you find those outside edge pieces of the puzzle that frame the big picture, by being inquisitive with the powers that be, asking where they see the firm going and what it is most likely to stumble on, and what worries them most about mergers or losing fee earners, or client audits or how profitable every partner is. Every conversation you have and every answer you get to that type of question will help you see where the technologies you are advocating for address real business challenges. And you’ll have a good context for talking with management about that next project. It shows that you are not just saying “There’s a really cool new technology that we just have to have!”

And I’d go a step further, to use some of what Lisa Bodell talked about in her keynote at ILTACON 2018 - Analyze how to put your IT department out of business, ask questions that expose your weaknesses and then you can design a plan to overcome those vulnerabilities. Lisa says, “Want better ideas? Ask better questions.” Don’t be afraid to ask anyone who will answer, do they consider your last IT project a success, and why or why not? The answers to that question will amaze you if you look at them in terms of how you can plan for real success in your next project.

On how you measure project success and when you measure it, see that as part of your need to look at risk assessment, quality assurance and defining success metrics at the beginning of the project and again in each project phase. Assuming you have answered the question around the business challenge the project is going to address, ask these kinds of questions:

  • Who needs to help define success? Is the technology going to be used by lawyers, other fee earners, professional staff, clients? Any and all of those should be involved in defining that success BEFORE the project is developed.
  • Does this technology rely on other existing systems or applications to work, or does it form a base for other technology to work from? Any point of contact needs to be identified early and plans made to ensure it plays well with others.
  • How will we test this technology? Traditional software testing occurs after the system is developed and before the users are exposed to it. What if the testing plan was created during the requirements phase, allowing the technical and end user testers to be involved in the objectives and requirements? Then the testing plan could be adjusted as the planning continues and the success metrics for the project are fleshed out.

If your first mistake was not asking the right question at the beginning of the project, don’t let your second mistake be waiting to ask questions until it’s too late, when you’ve developed the project and are now in the user pilot phase ready to deploy. By then you’ve accepted the risk of the project going forward and the boulder is rolling down the hill with nothing to slow it down. You can wait for it to crash or you can intervene to slow it down and make sure the path is clear.

Back to the question about the risk tolerance of your firm. To be innovative, you have to try things, and that means failing sometimes. Don’t be afraid to ask the questions in your organization about how well it can absorb project failure. The answers will help your focus on the front end of those projects, and build in the points at which you can turn back or abort, so you don’t end up with a system that is not adopted by users, or doesn’t work and needs to be rebuilt, or has to be abandoned. Put another way, is it more tolerable in your organization to fail a few times early in projects or fail spectacularly after a long, expensive process?

A final note on questions to ask around emergent technologies, the “trendy” projects. Everyone wants to be innovative, and an AI project is easier to sell these days than a document management upgrade. So, ask these questions and be honest with yourself about the answers you give:

    • Does this emergent technology hold real potential as a driver of future economic growth; will it increase productivity, or help launch new products and services?
    • Is this project being pursued because it sounds good to say you have something called AI? Is it really, really artificial intelligence?
    • Does this automation replace manual processes so that fee earners or professional staff can spend their time on more valuable work? Is there a real return on the investment and how long will it take to realize that return?
    • Is saying “We have an app for that?” important to your organization? Is building that app going to add real value for your users and/or clients?

A philosophical question to end on - how might we, and our legal technology organizations, change to embrace the positives from technology without being overwhelmed by the downsides? I welcome your thoughts and would like to continue this conversation, so log into the site and you will be able to add comments below.

Watch for the next installment of “Asking the Right Questions” when we think about how to ask the right questions around Innovation. 

LISTEN TO THE FULL INTERVIEW!

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TJ Johnson
 leads legal strategies for Olenick (www.olenick.com). She focuses on “StrategicIT” - conceiving and implementing new service lines to augment Olenick’s offerings, aligning with client engagements where her deep experience in legal technology helps deliver successful projects. A familiar and well-respected figure in the legal technology industry, TJ has worked in various capacities for law firms and legal departments. She is best known for her recent role on the executive team of ILTA (International Legal Technology Association) where she led the strategy development and execution of ILTA’s global portfolio of events, was instrumental in growing their premier conference, ILTACON, and was responsible for the vision and execution of many strategic projects.




  
Is the business challenge being addressed something the IT department defined or is it a fundamental business challenge of the firm, as outlined by management?

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