She'll inflate the cuff to a pressure higher than your systolic blood pressure, and it will tighten around your arm. Then she'll release it. As the cuff deflates, the first sound she hears through the stethoscope is the systolic blood pressure. It sounds like a whooshing noise. The point where this noise goes away marks the diastolic blood pressure.
As for when to check your blood pressure, the most important thing is to do it consistently the same time of the day (ask the doctor which time he prefers and also what time in relation to taking your medication). The following article has a lot of good information for someone just starting to monitor their blood pressure: https://www.drugs.com/cg/how-to-take-a-blood-pressure.html
Blood pressure refers to the force exerted by circulating blood on the walls of blood vessels and constitutes one of the principal vital signs. The pressure of the circulating blood decreases as blood moves through arteries, arterioles, capillaries, and veins; the term blood pressure generally refers to arterial pressure, i.e., the pressure in the larger arteries, arteries being the blood vessels which take blood away from the heart. 

High blood pressure, also known as hypertension (See blood pressure chart below) is called the “silent killer” for a reason — there are no obvious symptoms but it can result in heart attack, stroke and even death. The good news is there’s a lot you can do to maintain healthy blood pressure or get back to one, often without the need for medications.

Hypertension Stage 1 is when blood pressure consistently ranges from 130-139 systolic or 80-89 mm Hg diastolic. At this stage of high blood pressure, doctors are likely to prescribe lifestyle changes and may consider adding blood pressure medication based on your risk of atherosclerotic cardiovascular disease (ASCVD), such as heart attack or stroke.
Typically, more attention is given to systolic blood pressure (the first number) as a major risk factor for cardiovascular disease for people over 50. In most people, systolic blood pressure rises steadily with age due to the increasing stiffness of large arteries, long-term buildup of plaque and an increased incidence of cardiac and vascular disease.
High blood pressure, also known as hypertension (See blood pressure chart below) is called the “silent killer” for a reason — there are no obvious symptoms but it can result in heart attack, stroke and even death. The good news is there’s a lot you can do to maintain healthy blood pressure or get back to one, often without the need for medications.
The new guidelines stem from the 2017 results of the Systolic Blood Pressure Intervention Trial (SPRINT), which studied more than 9,000 adults ages 50 and older who had systolic blood pressure (the top number in a reading) of 130 mm Hg or higher and at least one risk factor for cardiovascular disease. The study's aim was to find out whether treating blood pressure to lower the systolic number to 120 mm Hg or less was superior to the standard target of 140 mm Hg or less. The results found that targeting a systolic pressure of no more than 120 mm Hg reduced the chance of heart attacks, heart failure, or stroke over a three-year period.
When your heart contracts and squeezes blood out into your network of arteries, the pressure inside those blood vessels is at its highest. This is called systolic pressure and it’s the top number on your blood pressure reading. In between beats, the heart relaxes and the pressure drops. This is your diastolic blood pressure, and it’s the reading’s bottom number.

The new guidelines stem from the 2017 results of the Systolic Blood Pressure Intervention Trial (SPRINT), which studied more than 9,000 adults ages 50 and older who had systolic blood pressure (the top number in a reading) of 130 mm Hg or higher and at least one risk factor for cardiovascular disease. The study's aim was to find out whether treating blood pressure to lower the systolic number to 120 mm Hg or less was superior to the standard target of 140 mm Hg or less. The results found that targeting a systolic pressure of no more than 120 mm Hg reduced the chance of heart attacks, heart failure, or stroke over a three-year period. 
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