For advertising agency CEOs, the period spanning major award submissions through the Cannes Lions festival represents one of the most concentrated periods of organizational intensity in the industry calendar. Award and pitch season arrive together in a way that is almost structurally inconvenient: the creative energy and leadership attention required to compete for business in a new pitch overlaps directly with the ceremonial and reputational demands of award season, and both overlap with the ongoing obligation to serve existing clients at the highest level.
No other period in the agency calendar places as many competing demands on the CEO simultaneously. The executives who navigate it well do so not through extraordinary endurance but through deliberate planning, effective delegation, and a clear understanding of where their time creates the most value.
This article examines how advertising agency CEOs can structure their time during award and pitch season to lead effectively across all three fronts: new business, industry recognition, and existing client service.
The Three-Front Challenge
Award and pitch season creates three simultaneous priorities for agency CEOs, each of which would be a significant time commitment on its own.
The first front is new business pitching. Major pitches that land during this period require CEO involvement at multiple stages: strategy alignment sessions, creative reviews, final presentation preparation, and sometimes the pitch itself. For a large agency with several active pitches, these commitments can consume 15 to 20 hours per week during peak pitch periods.
The second front is award submissions and recognition activity. Cannes Lions, the Effies, the Clios, and other major industry award shows require submission preparation, campaign documentation, and CEO participation in industry events, panels, and relationship activities. Award season is also a networking season; the conversations that happen at industry events often determine future business opportunities and talent relationships.
The third front is existing client service. Revenue is not paused during award season. Existing clients still need strategic counsel, campaign approvals, annual planning support, and the CEO-level relationship attention that keeps major accounts secure. The CEO who is visibly absent from key client relationships during a demanding period risks creating vulnerability in the agency’s revenue base.
Research from Deloitte on advertising industry performance consistently identifies leadership attention and client relationship quality as primary drivers of agency retention and new business conversion. During award and pitch season, both are under pressure simultaneously.
Establishing Pre-Season Priority Clarity
The most effective way to manage award and pitch season is to establish priority clarity before the season begins. This means making explicit decisions in advance about which pitches warrant CEO involvement, which award entries are most strategically important, and which existing client relationships require consistent personal attention during this period.
Not all pitches are equal. A CEO’s time in a pitch process has the highest return when the account is large, strategically important, or directionally significant for the agency’s positioning. Pitches for smaller accounts or accounts outside the agency’s strategic focus may warrant talented senior leadership involvement without CEO-level participation.
Similarly, not all award entries require CEO attention. The most strategically important submissions are those that, if recognized, would materially advance the agency’s creative reputation in a market the CEO is actively targeting for growth. These entries warrant the CEO’s direct involvement in submission framing and content. Others can be managed by the creative and strategy teams.
Mapping the Season in Advance
With pitch priorities and award priorities clarified, the CEO and executive assistant should map the entire award and pitch season on a single document four to six weeks before it begins. This map shows all confirmed pitches with their key milestones, all major award deadlines and events, all existing client commitments that are fixed, and any other significant calendar obligations.
Viewing the full season in a single document immediately reveals where conflicts exist, where time is genuinely overcommitted, and where buffer exists for opportunities that emerge during the season. It also enables the CEO to make proactive decisions about load management rather than reactive decisions under pressure.
Time blocking during award and pitch season works at the season level, not weekly. Weekly time blocking assumes a stable base schedule; during award and pitch season, the schedule is anything but stable, and planning must account for the full arc of the period.
Managing Pitch Process Involvement
For pitches where CEO involvement is warranted, a clear framework for how and when the CEO engages is more efficient than case-by-case decisions.
The CEO’s Role at Each Pitch Stage
At the brief intake and strategy stage, the CEO’s role is typically to align the pitch team on the agency’s strategic perspective on the client’s challenge and the creative direction that will distinguish the agency’s approach. This usually requires two to three hours: an initial strategy session and a follow-up review of the positioning before the team develops creative work.
At the creative development stage, the CEO’s role is reviewer and challenger rather than participant. Attending a full creative development session is less efficient than receiving a strong first-pass presentation and providing focused feedback in 60 minutes. Teams that know the CEO will review their work (rather than develop it with them) tend to produce more developed, more internally debated creative work before the review.
At the final presentation stage, the CEO’s direct involvement is typically most valuable. Being in the pitch room as the agency’s most senior leader sends a clear signal about the account’s importance and provides the credibility that a pitch team of junior and mid-level leaders cannot fully replicate. Preparation for this stage should include a full rehearsal the day before, even if the CEO has been close to the work throughout.
Protecting Existing Client Attention
One of the most common errors during peak pitch season is allowing new business preparation to crowd out existing client attention. The perception that the agency is too focused on chasing new business to serve existing clients is damaging to relationships that took years to build.
The CEO should maintain a short list of the five to ten existing client relationships that are most important to protect during award and pitch season. These relationships should receive consistent touchpoints (a brief check-in call, a handwritten note, or an in-person meeting if warranted) that signal the CEO’s continued engagement regardless of how intense the pitch calendar becomes. The executive assistant can manage the scheduling and preparation for these touchpoints, ensuring they happen reliably.
Award Season Engagement Strategy
Award season requires a different time model than pitch season. The time investment is less about creative engagement and more about relationship presence, industry positioning, and organizational morale.
Cannes Lions and Major Industry Events
Major industry events during award season carry significant strategic value for agency CEOs: relationship building with current and prospective clients, visibility with talent the agency is trying to recruit, and the organizational morale boost that comes from the agency’s leaders being visibly present at the industry’s recognition moments.
The strategic question is not whether to attend but how to be present most effectively. The most valuable Cannes activity for a CEO is typically a small number of high-quality private dinners and meetings rather than the full schedule of panels and parties that the festival makes available. Identifying the specific relationships that warrant dedicated time at Cannes, and ensuring those conversations happen, is more valuable than maximum attendance at public events.
EA delegation during award season handles logistics, keeping the CEO focused on key conversations.
Internal Award Season Leadership
Award season is also a morale moment for the agency’s creative team. Recognition at major shows validates the quality of the work and the creative culture the agency has built. The CEO’s internal visibility during award season, including attending submission reviews, celebrating wins publicly, and acknowledging the team’s effort in both victory and near-miss situations, matters for culture and retention.
This internal leadership dimension does not require significant time but does require presence at specific moments: the submission deadline all-hands, the announcement moment when results are released, and a brief recognition conversation with the teams whose work was submitted. Building these moments deliberately into the schedule ensures they happen without consuming the time needed for client and pitch activities.
Energy Management Across the Full Season
Award and pitch season is a marathon, not a sprint. The executives who perform best through the full period are those who manage their energy deliberately rather than relying on adrenaline and willpower to get through.
This means building recovery time into an intensive schedule: protecting sleep, maintaining exercise routines even during crunch periods, and identifying at least one day per week where the pace is genuinely lighter. It also means being selective about evening social commitments during award season. The agency CEO who attends every party will arrive at the pitch room the next morning in a worse state than one who makes selective, strategically motivated social choices.
The goal is sustainable performance across six to eight weeks rather than peak performance for one or two weeks followed by a crash that impairs the remainder of the season.
Post-Season Assessment
When award and pitch season concludes, a brief structured assessment of how the period was managed is one of the most valuable investments a CEO can make for future seasons. Key questions include: Which commitments generated the most value? Where was CEO time disproportionate to the return? Which delegation decisions worked well and which need adjustment? Were there early warnings about overload that the system should catch sooner next year?
This assessment, typically 60 to 90 minutes with the executive assistant and a chief of staff if present, produces concrete improvements that make the next award and pitch season more manageable and more productive.
Handling New Business Conflicts During Peak Season
One of the most difficult judgment calls during award and pitch season is how to handle new business opportunities that arrive after the season has already begun and the calendar is committed. Turning down business is never comfortable, but attempting to add a major pitch to an already full season calendar is a decision that affects more than the CEO’s schedule: it affects the quality of the pitch itself and the attention available to existing clients and award commitments.
Before agreeing to any new pitch commitment during peak season, the CEO and their EA should do a genuine capacity assessment. Is there a realistic path to executing this pitch at the level the client deserves, given the existing commitments? If the answer is uncertain, the more disciplined move is to be honest with the prospect about timing and propose a start date that falls after the peak season window. Prospects who respect the agency’s candor are better long-term clients than those who expect the agency to overcommit and then underdeliver.
For pitches that arrive during peak season and genuinely cannot wait, a modified pitch approach may serve better than a full-scale pitch. A chemistry meeting, a capabilities presentation, or a preliminary strategic response that positions the agency for a more complete pitch engagement after the season demonstrates genuine interest without the full resource commitment that a major pitch requires.
The Executive Assistant’s Specific Role During Award and Pitch Season
The demands on an executive assistant during award and pitch season are qualitatively different from normal operations. Understanding this distinction allows CEOs to brief their EA in advance and extract maximum value from the relationship when it matters most.
During award and pitch season, the EA’s primary function shifts from routine calendar and correspondence management to active flow management. This means proactively identifying conflicts before they become emergencies, ensuring that briefing documents are prepared before every CEO engagement, managing the logistics of pitch presentations and award event attendance, and maintaining a real-time view of where the CEO’s time is going against the pre-season priority map.
The EA should maintain a single master document during the season that shows all active pitches with their status and next CEO touch point, all award commitments with their deadlines, and all existing client touchpoints that are scheduled or overdue. This document, reviewed together in a brief daily check-in, is the navigation tool that keeps the CEO oriented during a period when the pace and complexity make it easy to lose track of competing commitments.
Brief your EA on your communication preferences specifically for this period. During normal operations, you may prefer email. During a major pitch crunch, direct messages on a high-signal channel may work better for urgent items. Make those preferences explicit before the season begins rather than adapting on the fly when speed matters most.
Conclusion
Award and pitch season is the most demanding period in an advertising agency CEO’s calendar precisely because it demands leadership across multiple high-stakes fronts simultaneously. The executives who navigate it effectively are not those who simply work harder during this period; they are those who plan earlier, delegate more effectively, and apply their personal time to the activities where CEO-level involvement is genuinely irreplaceable.
The result is an agency that wins more pitches, earns meaningful recognition, retains its best clients, and emerges from award season with its leadership team intact and its competitive position strengthened.
Related Reading
For further context, explore Time Management for CEOs Managing a Multi-Platform Media Strategy and Time Management for CEOs Managing Both Ad-Supported and Subscription Media Models.