Empowering Leaders at Pivotal Moments
I help leaders show up with alignment and intention when it matters most.
Through disciplined inquiry and strategic support, we help you lead with clarity.
I help leaders show up with alignment and intention when it matters most.
Through disciplined inquiry and strategic support, we help you lead with clarity.
At ASK Strategic Advisors we believe that clarity comes from asking
(and answering) better questions.
The right questions surface what matters most, align identity with actions,
and create space for intentional leadership.
The result is confident decision making and sustainable growth.
ASK Strategic Advisors is a boutique executive coaching and strategic advisory practice dedicated to helping leaders and organizations align who they are with how they show up. Founded by Ana R. Singletary - an executive coach and culture strategist - ASK creates spaces for leaders to realign, and reconnect with purpose. Through disciplined inquiry and reflective coaching, clients are guided to ask and answer the right questions - questions that surface clarity at the root and align identity, values and action.
The result is confident decision-making, intentional leadership and sustainable growth.
To help leaders strengthen self-awareness, clarify purpose, and translate that clarity into intentional action and lasting impact.
Aligning identity, values, and purpose with intentional, day-to-day action.
Recognizing, owning, and strategically leveraging your inherent strengths.
Using disciplined inquiry and evidence-based frameworks to turn reflection into clarity—and clarity into intentional action.
Ana Singletary is the Founder and Certified Executive Coach of ASK Strategic Advisors, Inc.
With over 25 years of experience across the financial services industry, Ana brings deep strategic credibility and real-world leadership perspective to her work. Her career spans executive leadership, talent and organizational development, employee engagement, and advising leaders through periods of growth and transformation.
Ana is known for her grounded, empathetic approach and her ability to create space for honest reflection while guiding clients toward meaningful action. Her coaching is rooted in inquiry, positive psychology, and evidence-based frameworks that help clients see themselves clearly, challenge limiting narratives, and align identity with how they lead and live.
Tools & Methodologies Include:
WAYS WE WORK TOGETHER
The ASK Strategy is centered on helping clients ask and answer the right questions that bring clarity at the root and support aligned, intentional action. Each engagement is tailored to each client’s context, goals, and stage of evolution. Whether you’re navigating a transition, leading through complexity or seeking greater alignment in how you show up, our work begins with thoughtful inquiry and moves toward purposeful progress.
A reflective coaching partnership that helps leaders gain clarity, deepen self awareness, and move forward with intention.
Offered in 1:1 and Small Group Coaching Formats
Strategic advisory support to help organizations align leadership, culture & business priorities.
Engaging talks and facilitated discussions that invite reflection and purposefull action.
Thoughtfully designed coaching engagements that help leaders reflect, recalibrate and move forward with purpose.
Clarify goals and define focus; great for short term problem solving
Deepen awareness and strengthen alignment; excellent for diving deeper
Embed purpose and sustain impact
Advisory and Speaking Engagements are shaped in response to the needs of each organization/audience with a focus on thoughtful leadership, shared understanding and practical insights.
When the right questions are asked, progress follows. Here’s how clients describe their experience with ASK Strategic Advisors.
Ana’s deep understanding of people, in particular women and women of color, in finance make her the perfect person to provide coaching in the sector. I think her 1:1 coaching is invaluable. As a 25 year veteran of Wall Street, I would have loved to have met Ana in the beginning of my career. I think her perspective and experience would be such an asset to any woman getting started in the NYC finance market. So, I hope she continues to increase her reach and impact to as many people as possible.
I can not recommend Ana highly enough. From our very first session, it was clear that she was an exceptional listener - fully present, thoughtful, and genuinely invested in understanding not only my professional challenges, but also the broader context, motivations, and values behind them. I consistently feel heard, respected, and supported, which creates a foundation of trust that allows for honest, productive conversations.
As a manager, I have encouraged several of my team members to seek thoughtful and purposeful coaching with ASK Strategic Advisors. As a result of Ana’s coaching, they are more cognizant about all facets of their work and have enhanced their leadership capabilities in meaningful and lasting ways.
Overall, working with Ana has been a powerful and transformative experience. Her blend of empathy, strategic insight, intellectual rigor, and practical guidance is exceptional. I have grown significantly in my self-awareness, leadership effectiveness, and career clarity, and I credit much of that growth to her skillful coaching. I would wholeheartedly recommend her to any leader navigating complexity, seeking greater autonomy and growth, or wanting a trusted partner to challenge and support them at the highest level.
Ana creates a coaching space that is both deeply reflective and highly strategic. Her ability to ask the right questions helped me to dig deeper, gain clarity, align my values with my leadership goals, and move forward with purpose. Each session left me more focused and empowered.
If you’re interested in a coaching, advisory, or speaking engagement please share a bit of context below. Every engagement begins with a thoughtful conversation.
