A few years ago I attended a terrific Chicago Crain’s Business annual breakfast panel of local General Counsels in the Chicago area. The panel moderator posed a question asking the panelists to share some best practices for in-house counsels when communicating with senior leaders and one of the panelists said that it’s important to “be brilliant, be brief and be gone.”

As an in-house lawyer, effectively communicating with your senior business clients and senior lawyers is a critical skill – especially since these senior leaders are very busy people with great demands on their time. Communicating in the right manner will help drive higher impact and demonstrate your “executive presence.” Here’s some best practices to embrace to help enable you to communicate better with senior leaders:

Move with Speed + Overcommunicate: In my experience there should always be a sense of urgency when communicating with senior leaders on high-profile matters – and to keep them well-updated on a going forward basis. This is especially important when the news you may need to communicate may not be positive or is highly sensitive in nature as no senior leader likes to be blindsided by potential issues. It’s always better to be proactive in communicating such news so these leaders are kept well informed and to “overcommunicate” when needed.

The Shorter the Better: When communicating via email with senior leaders, brevity is key. Several years ago, a former Microsoft CVP and Deputy General Counsel told us of his practice in sending emails to his senior business clients that were no longer than the screen of his laptop. Also think about adding crisp bullet points to your email, eliminate any “filler” words, always write economically and if you need to add more communication to your email simply add an attachment with more information as your email can provide an executive level overview.

Be Thoughtful and Not Sloppy: It’s also important to be very thoughtful in your communications with your senior leaders so don’t be rushed and take the necessary time to compose well-crafted and accurate digital communications like emails – and if needed, have someone else that you trust review those communications before you hit the send button. Also, keep two points top of mind before you send out an electronic communication: (1) what would your Chief Legal Officer think about it?; and (2) assume that it has the potential to appear on the front page of The Wall Street Journal.

Consistent Communication Cadence: Look for opportunities to have a consistent rhythm of recurring and pre-scheduled communications with key senior leaders. Perhaps it makes sense to have a weekly, monthly or quarterly 1:1 meeting with your most important senior business clients and/or senior leaders in your legal department. Also be sure to develop a short agenda for those meetings that you share in advance. In addition, it may make sense to provide a short and periodic report in the form of an “impact report” that you share with your senior leaders to depict the positive impact that you and your team are delivering to drive the business forward.

Capture their Attention: The first few words/sentences in any email to a senior leader is very important and is your opportunity to actively engage the leader in your message so use that space wisely. Also think about devising the proper subject matter of your message to your senior leader to help draw attention to your email. This early attention piece is also critical as there’s a good chance that senior leaders may be reading your email via a SmartPhone instead of a laptop device.

Embrace Bespoke Communications Styles: When communicating with senior leaders also adjust to their preferred communications styles. Some may prefer emails, others may prefer text messages, others may just prefer voice to voice communications, etc…Be sure to tailor your mode of communications to fit their specific needs.

High Impact Presentations: We will all have opportunities to deliver presentations to senior leaders. While of course you need to make sure to properly prepare for those presentations, in my experience with senior leaders I try to keep my presentations to no longer than 15 minutes in length maximum and to do it in a Ted Talk style format to make it as interesting and engaging as possible. Be sure to start strong in those presentations and don’t “PowerPoint people to death.” The fewer slides, with fewer words on those slides and the more interesting images on those slides that tells a story, the better.

Speak in their Language: As many of us know our business clients in Corporate America will often use their own business speak AKA “Corporate Speak” or company acronyms in how they communicate – and one of these days I do plan to post a blog about my all-time favorite “Corporate Speak” words/phrases. When communicating with your senior leaders think about opportunities to leverage their own “Corporate Speak” language and company acronyms so they can understand you better.

Decomplexify: When communicating with leaders – and especially business leaders – please avoid using legal terms or legal jargon (e.g., indemnify) that may serve to needlessly confuse them. Instead, break down complex legal subjects into clear and easy-to-understand messaging that even my 9 year old son can understand.

Provide a Recommendation: In your communications don’t forget to offer an actual recommended course of action or your view on the appropriate “next steps.” While your senior leaders are looking to you to keep them updated on particular matters, more importantly they need your guidance to help problem solve issues with speed and smart risk-taking.

Caution on Sensitive Communications: Remember that for very sensitive communications it’s probably smart to avoid sending out any emails or other electronic communications – especially since it may be increasingly difficult to preserve attorney-client privilege protections. In these situations please be sure to speak live with your senior leaders. If you do need to send out sensitive communications via email do your best to preserve attorney-client privilege, clearly mark those communications as “Confidential Information,” and also consider invoking the “Do Not Forward” email capabilities on your applicable email platform.

Use Email Delays: On occasion, we all make mistakes when crafting an email and hitting the send button. Think about configuring your email platform settings to delay the sending of an email so you have time to delete/edit it before it is formally sent.

Best of luck on your journey in communicating with impact to senior leaders. An in-house counsel’s ability to effectively communicate and influence others is increasingly important in our complex and fast-moving business environment.

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Photo of Dennis Garcia Dennis Garcia

Dennis Garcia is an Assistant General Counsel for Microsoft Corporation based in Chicago. He practices at the intersection of law, technology and business. Prior to joining Microsoft, Dennis worked as an in-house counsel for Accenture and IBM.

Dennis received his B.A. in Political…

Dennis Garcia is an Assistant General Counsel for Microsoft Corporation based in Chicago. He practices at the intersection of law, technology and business. Prior to joining Microsoft, Dennis worked as an in-house counsel for Accenture and IBM.

Dennis received his B.A. in Political Science from Binghamton University and his J.D. from Columbia Law School. He is admitted to practice in New York, Connecticut and Illinois (House Counsel). Dennis is a Fellow of Information Privacy, a Certified Information Privacy Professional/United States and a Certified Information Privacy Technologist with the International Association of Privacy Professionals. Please follow Dennis on Twitter @DennisCGarcia and on his It’s AI All the Time Blog.