Dale Chidester

Questioner

DISC Type : c

VP of Engineering at Microsoft

Leesburg, Virginia, United States

Overview

Dale is the VP of Engineering for Microsofts Specialized Cloud, focusing on engineering, operations, and security. His career is built on over 36 years of service supporting the U. S. Government, culminating in his role as Deputy CIO for Cyber Security and Operations at the CIA before joining Microsoft.

He appears passionate about mentoring and leveraging his professional network to create opportunities for others. Dale has publicly supported entry-level candidates seeking roles in the aerospace industry, showcasing a commitment to fostering new talent in the field.

After a 36-year career in public service that included the Army, White House, and CIA, he retired and immediately stepped into a VP role at Microsoft.

Personality Overview

Value Seeker

Not Easily Convinced

Price-Sensitive

While they don't hesitate to ask questions, they are generally risk-averse and tend to be late adopters. They generally do not appreciate an overfriendly approach and prefer to stay to-the-point. They are more likely than others to negotiate on pricing and terms.

Topics They Care About

Specialized Cloud Security

He leads engineering, operations, security, and compliance for Microsoft's Specialized Cloud, drawing from his deep expertise as the former Deputy CIO for Cyber Security at the CIA.

Government IT

Possesses decades of experience engineering and managing technology for critical U. S. government entities, including the CIA, White House, State Department, and DISA.

Career Transitions

He made a significant shift from a 36+ year career in government service to a senior executive role in the private sector with Microsoft.

Specialized Cloud Security: He leads engineering, operations, security, and compliance for Microsoft's Specialized Cloud, drawing from his deep expertise as the former Deputy CIO for Cyber Security at the CIA.

Government IT: Possesses decades of experience engineering and managing technology for critical U. S. government entities, including the CIA, White House, State Department, and DISA.

Career Transitions: He made a significant shift from a 36+ year career in government service to a senior executive role in the private sector with Microsoft.

Media Appearances

Dale has no verified media appearances

Work History

12-2025

VP of Engineering at Microsoft

5-2022 - 12-2025

Deputy Chief Information Officer - Retired at Central Intelligence Agency

2007 - 1-2022

Engineering Manager at Central Intelligence Agency

1998 - 2007

Field Manager/Professional Services at Lucent/Avaya

5-1997 - 1998

Video Engineer at DISA

Education

Dale has no verified education history

More Information

Social Presence :

Prographics :

Exp : 36 Location : Leesburg, Virginia, United States Job Level : Senior Designation : VP of Engineering at Microsoft

<div class="break-inside-avoid"><h1 class="sect-head" style="display:inline-flex; align-items:center"><div data-toggle="tooltip" data-placement="bottom" title="" data-original-title="DISC profile is one of the most popular behavioral assessment frameworks in use. It is especially useful in understanding workplace behavior and how different people approach similar situations differently.">DISC Profile : Dale's Key Traits </div></h1><div class="disc_main personality_container" style="display: flex;align-items: center;justify-content: center;"><figure class="highcharts-figure"> <div class="frrole_circle_label" style="position: absolute;top: calc(50% - 67.5px);left: calc(50% - 66.5px);">c</div> <div data-toggle="tooltip" data-placement="bottom" title="" data-original-title="Dominance(D) reflects how goal and task oriented a person is and her ability to accomplish results, irrespective of how demanding the circumstances might be. Those scoring high tend to be motivated by winning, competition and success and can be described as direct, demanding and strong willed." style="position: absolute;top: -4%;left: calc(50% - 20px);z-index: 2;cursor: pointer; border-radius: 50%; color:#fff;background: linear-gradient(360deg, #f1828d, #d2527f); height: 30px;width: 30px;font-size: 14px;align-items: center;justify-content: center;display: flex;font-weight: bold;opacity:1">D</div><div class="disclabel1" data-toggle="tooltip" data-placement="bottom" title="" data-original-title="Influence(I) reflects the degree to which a person prefers to work by influencing or persuading others. Those scoring high tend to be people oriented, are motivated by social recognition and building relationships and can be described as warm and enthusiastic in general." style="position: absolute;right: 5%;top: calc(50% - 20px);z-index: 2;cursor: pointer; border-radius: 50%; color:#fff;background: linear-gradient(270deg, #fad859, #f7ca18); height: 30px;width: 30px;font-size: 14px;align-items: center;justify-content: center;display: flex;font-weight: bold;opacity:1">I</div><div data-toggle="tooltip" data-placement="bottom" title="" data-original-title="Steadiness(S) reflects the degree to which a person is likely to focus on cooperation, support and taking everyone along. Those scoring high tend to be consistent and calm, are excited about the opportunity to collaborate and partner and could sometimes be indecisive or overly accommodating." style="position: absolute;bottom: -4%;left: calc(50% - 20px);z-index: 2;cursor: pointer; border-radius: 50%; color:#fff; background: linear-gradient(180deg, #b7f4d8, #66cc99);height: 30px;width: 30px;font-size: 14px;align-items: center;justify-content: center;display: flex;font-weight: bold;opacity:1">S</div><div class="disclabel2" data-toggle="tooltip" data-placement="bottom" title="" data-original-title="Calculativeness(C) reflects the degree to which a person is likely to be cautious, systematic and analytical. Those scoring high tend to emphasise quality and accuracy, enjoy showing off their expertise or challenging assumptions but can sometimes overanalyze things and be overcritical." style="position: absolute;left: 5%;top: calc(50% - 20px);z-index: 2;cursor: pointer; border-radius: 50%; color:#fff; background: linear-gradient(90deg, #848ccf, #524eb7);height: 30px;width: 30px;font-size: 14px;align-items: center;justify-content: center;display: flex;font-weight: bold;opacity:1">C</div><div style="position: absolute;top: calc(50% - 106.5px);left: calc(50% - 106.5px);border-radius:50%;border: 1.5px dotted #c8c6c6;padding:105px"></div><div style="position: absolute;top: calc(50% - 135.5px);left: calc(50% - 135.5px);border-radius:50%;border: 1.5px dotted #c8c6c6;padding:133px"></div> <div id="disc_container"></div> </figure><div class="row traits-row" style="position: relative;width:70%;justify-content:flex-end;margin-right:10px"><div class="personality-cards col-md-10"><div class="personality-head">Calculativeness</div>Calculativeness(C) reflects the degree to which a person is likely to be cautious, systematic and analytical. Those scoring high tend to emphasise quality and accuracy, enjoy showing off their expertise or challenging assumptions but can sometimes overanalyze things and be overcritical.</div></div></div></div><div class="break-inside-avoid"><h1 class="sect-head" style="display:inline-flex; align-items:center"><div data-toggle="tooltip" data-placement="bottom" title="" data-original-title="OCEAN personality assessment, or Big 5 personality traits model, is the second most well-known behavioral assessment framework after MBTI. It provides a holistic way of understanding how people are and what to expect of them.">OCEAN Profile : Dale's Key Traits </div></h1><div class="ocean_main personality_container" style="display: flex;align-items: center;justify-content: center;"><figure class="highcharts-figure"> <div class="frrole_circle_label" style="position: absolute;top: calc(50% - 67.5px);left: calc(50% - 66.5px);">Noa</div> <div data-toggle="tooltip" data-placement="bottom" title="" data-original-title="Openness(O) reflects the degree of intellectual curiosity, a desire to seek new experiences and a preference for novelty and variety. Those scoring high tend to be inventive, curious and open to trying new things whereas those scoring low tend to be consistent, cautious and more realistic in their approach." style="position: absolute;top: -7%;left: calc(50% - 12px);z-index: 2;cursor: pointer; border-radius: 50%; color:#fff; background: linear-gradient(90deg, #963694, rgb(175,79,173));height: 30px;width: 30px;font-size: 14px;align-items: center;justify-content: center;display: flex;font-weight: bold;opacity:0.72">O</div><div data-toggle="tooltip" data-placement="bottom" title="" data-original-title="Conscientiousness(C) reflects the degree of self-discipline, focus on doing things in a planned manner and acting dutifully. Those scoring high are usually efficient, organized and focused whereas those scoring low tend to be easy-going, spontaneous and unreliable at times." style="position: absolute;right: 4%;top: calc(50% - 70px);z-index: 2;cursor: pointer; border-radius: 50%; color:#fff; background: linear-gradient(180deg, #f15a22, rgb(255,115,59));height: 30px;width: 30px;font-size: 14px;align-items: center;justify-content: center;display: flex;font-weight: bold;opacity:0.72">C</div><div data-toggle="tooltip" data-placement="bottom" title="" data-original-title="Extraversion(E) reflects the degree of assertiveness, sociability that an individual exhibits. People scoring high on extraversion tend to be outgoing, energetic and talkative whereas those scoring tend to be reserved, quiet and thoughtful, especially in social settings." style="position: absolute;bottom: 3%;left: calc(50% - -93px);z-index: 2;cursor: pointer; border-radius: 50%; color:#fff; background: linear-gradient(270deg, #bf55ec, rgb(216,110,255));height: 30px;width: 30px;font-size: 14px;align-items: center;justify-content: center;display: flex;font-weight: bold;opacity:0.72">E</div><div data-toggle="tooltip" data-placement="bottom" title="" data-original-title="Agreeableness(A) reflects the degree of compassion, cooperation and general friendliness in a person. Those scoring high are mostly even-tempered, pleasant and easy to convince whereas those scoring low tend to challenge and question things and are likely to have a contrarian attitude." style="position: absolute;left: 17%;top: calc(50% - -127px);z-index: 2;cursor: pointer; border-radius: 50%; color:#fff; background: linear-gradient(360deg, #be5683, rgb(215,111,156));height: 30px;width: 30px;font-size: 14px;align-items: center;justify-content: center;display: flex;font-weight: bold;opacity:0.72">A</div><div data-toggle="tooltip" data-placement="bottom" title="" data-original-title="Emotional Stability(ES) refers to the degree to which one can experience unpleasant emotions like anger, anxiety etc. easily. Those scoring high tend to be calm, stable and are not perturbed easily whereas those scoring low can be passionate, excitable and have low impulse control, especially under stressful circumstances. (Emotional Stability is same as Neuroticism rated on a reverse scale)" style="position: absolute;left: 5%;top: calc(50% - 70px);z-index: 2;cursor: pointer; border-radius: 50%; color:#fff; background: linear-gradient(360deg, #f62459, rgb(255,61,114));height: 30px;width: 30px;font-size: 14px;align-items: center;justify-content: center;display: flex;font-weight: bold;opacity:0.72">N</div><div style="position: absolute;top: calc(50% - 106.5px);left: calc(50% - 106.5px);border-radius:50%;border: 1.5px dotted #c8c6c6;padding:105px"></div><div style="position: absolute;top: calc(50% - 135.5px);left: calc(50% - 135.5px);border-radius:50%;border: 1.5px dotted #c8c6c6;padding:133px"></div> <div id="ocean_container"></div> </figure><div class="row traits-row" style="position: relative;width:70%;justify-content:flex-end;margin-right:10px"><div class="personality-cards col-md-10"><div class="personality-head">Emotional Stability</div>Emotional Stability(ES) refers to the degree to which one can experience unpleasant emotions like anger, anxiety etc. easily. Those scoring high tend to be calm, stable and are not perturbed easily whereas those scoring low can be passionate, excitable and have low impulse control, especially under stressful circumstances. (Emotional Stability is same as Neuroticism rated on a reverse scale)</div><div class="personality-cards col-md-10"><div class="personality-head">Openness</div>Openness(O) reflects the degree of intellectual curiosity, a desire to seek new experiences and a preference for novelty and variety. Those scoring high tend to be inventive, curious and open to trying new things whereas those scoring low tend to be consistent, cautious and more realistic in their approach.</div><div class="personality-cards col-md-10"><div class="personality-head">Agreeableness</div>Agreeableness(A) reflects the degree of compassion, cooperation and general friendliness in a person. Those scoring high are mostly even-tempered, pleasant and easy to convince whereas those scoring low tend to challenge and question things and are likely to have a contrarian attitude.</div></div></div><hr class="divider-hr" style="margin-bottom:20px"></div>

Dale Chidester

VP of Engineering at Microsoft

Leesburg, Virginia, United States

Overview

Personality Overview

Topics They Care About

Media Appearances

Work History

Education

More Information

Social Presence :

Prographics :

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Insights For Selling To Dale

During A Call Or A Meeting

When Cold Calling

Pattern Interrupt: Speaking in a slightly hesitant manner, and seeking their permission at the start through a negation can get you a chance.

Pace: Speak slightly fast, especially if you tend to be calm and confident. Sound like a ‘knows their domain’ person.

Tone: Keep your tone slightly apprehensive, as if you are a little unsure about calling them.

Tactics To Win: Use of negations, giving full information

Mistakes To Avoid: Use of superlatives, overusing social proof

Making The Ask: Use negations, it is extra effective with them. It gives them a chance to say no, they like doing that.

Subconscious Driver: They believe they know a lot, so it needs to make sense as well as make them curious. They need to think that it is something worth investigation.

Greeting: Hi Dale, this is [user_fname] at [user_companynamefirsttwowords].

Opener: You probably don’t want to be on this cold call, would it be a problem if I asked for 30 seconds of your time?

Introduction: My company has leveraged 30+ years of research to build an AI that can predict anyone's personality, behavior and decision-making style before you even spend a minute with them.

Ask: Companies like [abc], [xyz] have been able to move [KPI1] by X% and [KPI2] by Y%. Would it be too much to put 15 minutes on your calendar to share why this could be high ROI for you?

Close: Can I suggest [time1] on [date1]? Or would you prefer any other slots? And [prospect_email] would be the right email ID for you?

When Writing An Email

Subject: Objective

Salutation: Yes ( Something usual)

Greeting: No

Emojis/GIFs:

Bullet Points: Recommended

Closing Line: Logically summarize/ask

Complimentary Close: None or formal

Tone of Words: Objective, informational

Overall Messaging: Focused on allaying doubts and ROI

Length of Mail: Short

While Negotiating & Closing

The secret to closing fast with Dale is

Will you ever get a clear answer from Dale

Insights For Deal Planning

How fast (or slow) will Dale move?

Can Dale take some risk or not?

You And Dale

Personality Compatibility

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