What to do when you step into a new leadership role.

1. Executive Leadership Playbook
Hawkins.Rosevelt@gmail.com
PH: 512-619-1049

2. ATrue Leaders Mindset

3. Mindset for Success
While the average tenure of a new sales leader ranges from about
19 to 24 months, the turmoil it causes across an entire organization
is painful when you have to replace them.
It’s important to remember that all organizations are unique and
each one poses its own extraordinary challenges for transition
As a leader, I get extremely excited about observing a companies
challenges, analyzing their situation and discovering the
opportunities. The only way to strategize accordingly is to properly
analyze to the best of your ability. (Lead Velocity, ASP, ACV, Sales
Cycle, Pricing Model, Target Buyer, LTV, CAC)
As my corporate blueprint has remained consistent at multiple
organizations, my plan would be simple. I always start by
connecting with the people on the inside to make a difference to the
companies and people on the outside. (Executive, Sales,
Marketing, Customer Support, Ops, Product, Finance, and
Engineering)
As a new sales leader, I would start from ground-zero irrespective
of my corporate credentials. As it’s upon me as the new sales
leader to gain trust, build credibility, become an asset and
accelerate the transition.
It’s critical that a strong foundation is laid with a defined framework
in the first quarter for long-term success.
True transition is about the entire company and not the new
sales leader

4. Pillars for Success
PEOPLE
CULTURE
PRODUCT/SOLUTIONS
CUSTOMER
OPERATIONS/PROCESS
COMMUNICATION

5. Get to know the Executive Leadership: Understand the team and
perceptions of key stakeholders. Gather their expectations and learn
their communication styles.
Get to know immediate team: Provide Q&A and background on my
journey. Execute 1:1’s. Gather individual personas, roles, goals, skills,
past and current performance as well as morale level. Get the pulse of
the team. (Positive and Negative) Build consensus.
Get to know vitality of team: High performers, potential change reps,
recruitment and hiring. Find the disablers. Competency assessments.
Get to know Finance: Understand current compensation models,
incentives, recognition programs, spiffs, allotted budgets and all awards
Get to know the companies customer: Identify client DNA – Marketing
Qualified Lead (MQL)
Get to know Marketing team: Identify the people behind the machine.
Build strategic relationships and understand what drives the client
interaction.
Watch, Ask, Listen and Learn
People

6. Culture
Every organization has a distinct culture.
As a new sales leader my role would be to comprehend the
company culture and take deliberate steps to learn the
hierarchies and adapt.
Critical Elements:
Understand the formal and informal ways of information
exchange within the company
Understand and adapt to how things get done
Ensure my leadership and management style is in harmony
with the common culture

7. Product/Solutions
Understand companies client life cycle.
Understand the current product/solution and the sales
positioning
Review the product features, architecture and benefit with
teams/people
Study the website
Get in the trenches, learn the process of selling and take
ownership
Identify the tools needed to see success in the role
Understand what has worked well in the past and currently
versus what has not worked well
Facilitate brainstorming sessions with sales team

8. Get familiar with the industry/marketplace
Talk to sales reps and understand value proposition
Understand Customer Triggers
Understand the customer segments and the company value
proposition
Understand client objections to solution
Understand the competition
Understand how company views customer engagement
Understand customer satisfaction survey
Understand client onboarding process
Review product training knowledge
Customer

9. Understand and familiarize myself with existing systems and
review the current state of business.
Understand the following processes:
Recruiting – Hiring – Onboarding
Training and Ongoing Development
Quality Assurance
Product Development Life Cycle – Product updates
Quota Setting – Sales – Client Support – Chargebacks
Performance Improvement plan
Department transfers – Promotions – Terminations
Compensation Tracking Process
Operations/Process

10. Understand companies current communication modes,
methods and practices of etiquette within the organization.
Understand the communication requirements and standard
operational steps required for processes involved.
Communicate the playbook strategy clearly to my immediate
team and senior management.
Encourage cooperative communication within the team to
promote equal idea exchanges and wider acceptance
Tailor specific messages of communication to specific groups
appropriately.
Develop standard communication on the goals that drive
higher performance. (Metrics, KPI’s, Workflow)
Communication

11. Tactical Breakdown

12. 30 – 60 – 90 Timeline
First 30 Days
During my first thirty days of tenure, I will not look to implement
any major changes. Without internal-buy in, any changes have
a high chance of failure. Plus, its mandatory to understand the
team and processes.
Get to know companies people and business
I will use my time to get a feel for the companies environment;
building rapport with the team, and developing a
comprehensive understanding of how the team operates. This
would include meeting all my direct reports as well as other
department heads. Doing this will allow me to get acquainted
with the company culture, state of the business and the
motivation of my direct reports.

13. 30 – 60 – 90 Timeline
First 30 Days
It’s imperative that I demonstrate to the company sales team
that I’m willing to get into the trenches. I have to go through
training and join them on sales calls. This will enable me to
understand the sales process and ramp faster. There’s
nothing like leading by example.
I will work with executives, managers and department heads
and gather their opinions on the highest priorities in the
organization, so I can understand alignment and disconnects.
This will allow me to focus on data and how it works within the
performance matrix.
My next step would be to assess the sales department’s
success and challenges. My emphasis will be placed on
reviewing historical data regarding pipeline’s performance.
Gathering specifics of team pipeline and individual
performance metrics will give me the ability to understand how
to drive sales performance.
Stay in learning mode.

14. 30 – 60 – 90 Timeline
Create my vision: Days 30-60
This is the window in time whereas I will start formulating/building
my long-term vision for the sales team while knocking out a few
easy wins.
Build consensus
While I’m devising plans, I will consult with sales representatives
at every step. Their reactions are critical for determining how I will
go about implementing change. If I’m planning a major initiative,
it’s helpful to have other members of the sales team advocate for
my plans. Involving them in the changes will allow them to feel a
personal connection and easily adapt.
Executive support
In creating my vision I will listen to my executive team. Having
their suggestions and incorporating their feedback will do much to
establish unity and alignment across the organization.

15. 30 – 60 – 90 Timeline
Create my vision: Days 30-60
Build credibility by going after quick wins
Throughout my second month, I will continue to lead by example
and earn credibility in the eyes of the sales team. At this point
more of my time will be spent on strategic planning and
organizational design.
If I’ve correctly utilized my first 30 days, this is the time to take on
one or two initiatives. I will seek some quick wins. Everyone
knows that early success is critical when trying to establish
credibility.
I need to establish a core understanding of the key metrics in
order to measure the success of my plan. In some cases, I may
need to define the metrics that I want to monitor in case the plan
isn’t going well so adjustments can be made quickly. Once the
new strategies are implemented, I will closely monitor the metrics
quantitatively and qualitatively.

16. 30 – 60 – 90 Timeline
Delegate tasks
At this point I should have a fairly decent rapport with the sales
team and a better idea of where strengths lie with specific team
members. This gives me the power to delegate effectively. This
is a very important step as it will be important to delegate and
gain leverage. So I will use my new found knowledge and
assign tasks to people interested in certain tasks. The perfect
assignment is one that aligns individual strengths with interests.
Continue to build consensus and listen to feedback
The best way to start in a new leadership role is to over-
communicate and keep everyone on board with the plan. I will
check in with my team members regularly and be conscious of
prioritizing people. The key will flow through listening to
everyone. As I gain momentum on execution, I will start tackling
more ambitious initiatives.
Orchestrating change is in how you treat people and the how
you align every area of the business.

17. Critical Needs
Critical Needs
A plan means nothing without having critical pieces of current
data. The following list will ensure a clear “lay of the land” view,
and make for a smooth transition.
Summary of your key accountabilities and KPI’s
Sales Process
CRM Overview – Provide a view of the pipeline, the sales process,
forecasting and the CRM tool being used.
Compensation – Overview of compensation models and exception
handling. Include attainment distribution, payout averages, ranges
by role, industry benchmarks and cost verses budget.

18. Critical Needs
Critical Needs
Quota Setting Process
Sales Territory Design / Structure Process
On-Boarding – Summary of process for onboarding, training
modules, technology set-up, etc.
Job Descriptions and Scorecards by role
Competitive Landscape
Sales & Marketing Alignment – Lead Generation, Management,
Nurturing and Handoff. Shared KPI’s, etc.
Executive Growth Plan

19. https://www.linkedin.com/in/rosevelt-hawkins-3202b74b/