Senior leaders today navigate a world of constant disruption. They need to guide their organizations toward a thriving future, yet they are bombarded with short-term pressures and an ever-changing landscape. Sound familiar?

This week’s post is for you – the strategic mind, juggling long-term vision with the business imperative to achieve immediate results.

We delve into insights shared by 40 senior executives and chief strategy officers at last week’s Outthinker Networks Summit in Miami, focusing on three critical areas:

  • Integrating AI into strategic conversations: Explore how AI can augment your team’s capabilities, while uncovering the key considerations for effective human-AI collaboration.
  • Cultivating long-term vision amidst short-term pressures: Discover strategies to navigate the tension between immediate needs and long-term vision, even in a fast-paced environment.
  • Measuring the success of your strategy office: Learn from a best-in-class example and discover a valuable metric to gauge the impact of your strategy function.

Ready to unlock strategic agility and propel your organization forward? Read on to discover actionable insights from your peers. 

Integrating AI into strategic conversations 

Most AI discussions revolve around productivity and workflow, but there is an even greater challenge to solve: How does the use of AI impact how teams interact? And what changes do we need to make for humans to improve teaming with AI?

In the first session of the summit, Valery Yakubovich, executive director of the Mack Institute for Innovation Management at The Wharton School, led a workshop to test the hypothesis: Can AI be a true participant in strategy discussions?

Most attendees agreed that an AI assistant would be a useful tool on a strategy team, but how would that impact team dynamics in practice?

Valery divided summit participants into groups of six, assigning roles to each group member:

  • Two AI-free subject matter experts (SMEs), relying on their own knowledge and experience.
  • Two AI-augmented humans, using their large language model (LLM) of choice.
  • One “robot,” agreeing to input prompts exactly as given and to share responses directly from the LLM (robots used ChatGPT across groups).
  • One observer, taking note of group dynamics to determine which roles contributed the most and which commanded the most attention from the group.

The Assignment: Act as managing partners in a global consulting firm tasked with reinventing the firm’s business model considering the advent of Generative AI, with a particular focus on LLMs. The team was instructed to harness its diversity of sociodemographic backgrounds, experiences, and perspectives to forge an innovative business model. Members would complete the Business Model Canvas to share their outputs and reconvene with the broader summit group after 50 minutes.

AI’s seat at the strategy table 

The learnings from the session highlighted an underappreciated aspect of how AI gets involved in human decision making.

When the groups came back together, Valery facilitated observation sharing from each participant. There was a consensus among groups – the third observation was the most interesting:

  1. The top contributor was either the unassisted human SME or the AI-augmented SME.  
  2. The “robots” were not used very often. In one group, 15 minutes went by without prompting the LLM.
  3. The mode of communication made a difference. While the AI-driven and AI-augmented team members were typing in prompts, the human discussion had already moved on. When it was time to share responses, the LLMs and LLM-assisted humans lagged behind.

The discussion resulted in a few key findings:

  • The AI and AI-augmented team members generated useful information, but there was a loss of fluidity in ideation and conversation. Companies, designers, and innovators need to figure out a new form of multimodal interaction with AI, one that includes sharing multiple screens and implementing voice technology.
  • The AI-augmented team members with more experience in prompt engineering and translating outputs were more successful at seamlessly participating in the discussion. Well-trained and practiced humans-in-the-loop will become “superheroes.”
  • True teaming with AI requires disarming mental blocks. Subject matter experts should practice an element of “beginners mind,” assuming they might be lacking in information or ideation, and ask AI to fill in any gaps. One group adjusted for this by asking: “SME can you add anything to the LLM response?” and “LLM can you add anything to the SME response?” When the answer was no, they moved on.


AI presents new questions and opportunities for communicating in teams. In team communication, information gets transferred and downloaded, and a response is chosen.

Consider a football team deciding its next play. They need to share and debate ideas, review proposals, and decide in that moment. Most companies have been thinking about the time before the game—incorporating generative AI into strategic planning. But where AI will really shine is in the moment. When the quarterback is sacked, or the pass is fumbled—what should each member of the team do next? And how do they do it as quickly as possible?

When it’s time to decide, companies must be ready to leverage AI with agility. Prepare for this by considering how often and how effectively you incorporate AI into meetings. Is your organization giving AI a seat at the table yet?

Cultivating long-term vision amidst short-term pressures 

Everyone agrees that strategy is important, so why does almost no one make time for it?

Bestselling author and top-ranked global management thinker Dorie Clark began the next session with a revealing yet unsurprising statistic: According to a study of 10,000 senior leaders done by Management Research Group, 97% of respondents said more strategic thinking would make the greatest difference for the company. A separate study found that 96% of leaders don’t have time for strategic thinking. Companies are driven by shareholder expectations to meet quarterly results.

Strategy leaders are feeling the pressure. They walk the tightrope between short and long term in a landscape that is pushing more and more to the near term. CSOs must look to a two- to three-year horizon and advise on trends that have not yet proven their value.

For example, Generative AI appeared to shock the world at the end of last year. But a strategist recognizes that exponential technologies and inflection points show signs around the edges before they occur. Outthinker Networks Advisory Board member Rita McGrath calls this “seeing around corners.”

Dorie explained, “The average observer will see a trend and say it’s never going to happen for years. For strategists, things can be ‘never going to happen’ for a very long time, even decades. Then all of a sudden there’s an exponential leap that shows everyone what’s possible.”

In an organization looking for results in the next quarter, this can present a frustrating roadblock. One attendee noted, “As a CSO your ability to play the long game, experiment, or even think innovatively is directly related to the CEO.”

Another added, “It’s not even the CEO. It’s shareholders. How can CSOs take accountability and not just follow what we’re told to do?”


Outthinker Networks members offered some recommendations for strategic minds to persevere through short-term thinking:

  • CSOs should look to achieve and measure small, tangible wins, then become good internal marketers to announce those wins to leadership teams.
  • Remember that companies usually need to invest in 100 projects to develop one that is groundbreaking for the company. Turn experiments into success stories by shifting expectations. What if the purpose of an experiment were not to solve the problem, but to generate new insights?
  • Organizations require patient capital to be able to focus on the long term. One member suggested that a shift toward ecosystem business models could lead to finding investors in unexpected places. “We are a financial services company and one of our top investors is a media company playing the long game for access to our customers,” he shared. Consider also that in today’s environment of higher interest rates and tight financial markets, private equity firms are taking longer to exit their investments.

A metric to measure the success of your strategy office

Most companies we talk to either don’t know how to measure the success of their strategy office, or they measure things like new revenue or margins. But there is an overlooked and highly valuable role that your strategy office could play: nurturing talent for your organization. 

The next session of the day was led by the strategy team of our event host, Southern Glazer’s Wine & Spirits (SGWS). Outthinker Networks member and SGWS CSO Stephen Von Oehsen and a panel of his team members offered a behind-the-scenes look into what it takes to build a best-in-class strategy office that has grown in its impact over two decades.

They use an indicator of success that might be helpful in measuring your organization’s strategy function: training strategic skills to infuse into the organization.

Thus far, the SGWS Office of Strategic Management (OSM) has integrated 20 of its professionals into leadership roles across the organization. The strategy office has become a springboard into the business, because the strategy function introduces employees to high visibility, a rotation of projects, and relationships to leaders across the company. This gives them the ability to operate successfully when they move into a new role – if they choose to; over two decades, the SGWS OSM has achieved an 85% retention rate and less than 1% attrition.

To determine the success of your strategy function, consider how much the rest of the organization desires your talent.

Final thoughts 

We left the session realizing there are three expanded opportunities and possibilities the strategy office can deliver that many organizations are not yet aware of: Using AI to have better strategic conversations, pushing the organization to think long term, and attracting and cultivating top talent. Companies that leverage CSOs and balance long-term vision with short-term necessity will come out ahead and be better prepared for the challenges of the future.

Outthinker Networks is a global peer group of heads of strategy, innovation, and transformation at $1B+ companies who are determined to move their organizations to the next level. Members engage in curated learning, practical conversations, and networking opportunities to be more successful in performing their roles, solving their top challenges, and keeping their organizations ahead of the pace of disruption. APPLY TO JOIN.